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Provided is a hydroxyl-protected alcohol of the formula R--O--Pg, wherein Pg is a protecting group of the formula: wherein Y, Z, W, R1, R1a, R2, R2a, R3, R3a, R4, R4a, a, b, c, d, e and f are defined herein and R is a nucleosidyl group, an oligonucleotidyl group with 2 to about 300 nucleosides,

Provided is a hydroxyl-protected alcohol of the formula R--O--Pg, wherein Pg is a protecting group of the formula: wherein Y, Z, W, R1, R1a, R2, R2a, R3, R3a, R4, R4a, a, b, c, d, e and f are defined herein and R is a nucleosidyl group, an oligonucleotidyl group with 2 to about 300 nucleosides, or an oligomer with 2 to about 300 nucleosides. Also provided is a deprotection method, which includes heating the hydroxyl-protected alcohol at a temperature effective to cleave thermally the hydroxyl-protecting group therefrom.

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The invention claimed is: 1. A hydroxyl-protected alcohol of the formula R--O--Pg, wherein Pg is a hydroxyl-protecting group of the formula: wherein: Y is R1, OR1, or NR1R1a; Z is O, NR2 or CR2R2a; W is CO; R1, R1a, R2, R2a, R3, R3a, R4 and R4a are the same or different and each is H, a saturate

The invention claimed is: 1. A hydroxyl-protected alcohol of the formula R--O--Pg, wherein Pg is a hydroxyl-protecting group of the formula: wherein: Y is R1, OR1, or NR1R1a; Z is O, NR2 or CR2R2a; W is CO; R1, R1a, R2, R2a, R3, R3a, R4 and R4a are the same or different and each is H, a saturated alkyl, an unsaturated alkyl, an aryl, a saturated alkyl with an aryl substituent, or an unsaturated alkyl with an aryl substituent, wherein: any of the alkyl-containing groups for R1, R1a, R2, R2a, R3, R3a, R4 or R4a is unsubstituted or substituted with one or more substituents, which are the same or different, and selected from the group consisting of a halogen, a saturated alkyl, an unsaturated alkyl, a hydroxyl, an alkoxy, an aryloxy, an aralkoxy, an alkyl carboxylate, an unsaturated alkyl carboxylate, an aryl carboxylate, an amide, a sulfhydryl, an alkyl sulfide, an aryl sulfide, an alkyl sulfoxide, an aryl sulfoxide, an alkyl sulfonyl, an aryl sulfonyl, an alkylcarbonyl, an unsaturated alkyl carbonyl, an aryl carbonyl an alkyl thiocarbonyl, an unsaturated alkyl thiocarbonyl, an aryl thiocarbonyl, a cyano, and a nitro; any of the aryl-containing groups for R1, R1a, R2, R2a, R3, R3a, R4 or R4a is unsubstituted or substituted with one or more substituents, which are the same or different, and selected from the group consisting of a halogen, a saturated alkyl, an unsaturated alkyl, a hydroxyl, an alkoxy, an aryloxy, an aralkoxy, an alkyl carboxylate, an unsaturated alkyl carboxylate, an aryl carboxylate, an amide, a sulfhydryl, an alkyl sulfide, an aryl sulfide, an alkyl sulfoxide, an aryl sulfoxide, an alkylsulfonyl, an arylsulfonyl, an alkylcarbonyl, an unsaturated alkyl carbonyl, an aryl carbonyl, an alkyl thiocarbonyl, an unsaturated alkyl thiocarbonyl, an aryl thiocarbonyl, a cyano, a nitro, an amino, an alkylamino and a dialkylamino; and optionally, R1 or R1a is attached to a solid support; a, b, c, d, e and f are the same or different and each is H, a halogen, a saturated alkyl, an unsaturated alkyl, a hydroxyl, an alkoxy, an aryloxy, an aralkoxy, a cyano, a nitro, a sulfhydryl, an alkyl sulfide, an aryl sulfide, an alkyl sulfoxide, an aryl sulfoxide, an alkylsulfonyl, an arylsulfonyl, an alkylcarbonyl, an unsaturated alkyl carbonyl, an aryl carbonyl, an alkyl thiocarbonyl, an unsaturated alkyl thiocarbonyl, an aryl thiocarbonyl, an alkyl carboxylate, an unsaturated alkyl carboxylate, an aryl carboxylate, an amide, an amino, an alkylamino or a dialkylamino; and R is a nucleosidyl group, an oligonucleotidyl group with 2 to about 300 nucleosides, or an oligomer with 2 to about 300 nucleosides; provided that Y is not OR1 when Z is O. 2. The hydroxyl-protected alcohol of claim 1, wherein Z is NR2. 3. The hydroxyl-protected alcohol of claim 1, wherein R2 is H or a saturated alkyl. 4. The hydroxyl-protected alcohol of claim 1, wherein Y is R1, wherein R1 is a saturated alkyl or an aryl. 5. The hydroxyl-protected alcohol of claim 1, wherein R3 and R3a are H. 6. The hydroxyl-protected alcohol of claim 1, wherein R4 and R4a are H, or one of R4 and R4a is H and the other is an aryl. 7. The hydroxyl-protected alcohol of claim 1, wherein Pg is selected from the group consisting of: 8. The hydroxyl-protected alcohol of claim 1, wherein R is of the formula: wherein: Q is a linking substituent selected from the group consisting of nucleosidyl group, an oligonucleotidyl group with 2 to about 300 nucleosides, and an oligomer with 2 to about 300 nucleosides; X is O, S or Se; R5 is H or a protecting group; R6 is H, a protecting group or a solid support; B is a labeling group, a saturated alkyl, an unsaturated alkyl, a cycloalkyl, an aryl, a heteroaryl with 5 to about 10 atoms, including at least one heteroatom selected from the group consisting of O, N, S, an oxide of N, and an oxide of S in the ring skeleton thereof, a heterocycloalkyl with 3 to about 10 atoms, including at least one heteroatom selected from the group consisting of O, N, S, an oxide of N, and an oxide of S in the ring skeleton thereof, a saturated alkyl with an aryl substituent, an unsaturated alkyl with an aryl substituent, an amino, an alkylamino, a dialkylamino, a purinyl, a pyrimidinyl, adeninyl, guaninyl, cytosinyl, uracilyl, or thyminyl, wherein B is unsubstituted or substituted with one or more substituents, which are the same or different, selected from the group consisting of a nucleobase protecting group, R7, OR7, NHR7, NR7R8, N═CH--NR7aR8a,N═C(alkyl)-NR7aR8a , CN, NO2, N3, and a halogen, wherein R7 and R8 are the same or different and each is H, a saturated alkyl, an unsaturated alkyl, an alkylcarbonyl, an unsaturated alkyl carbonyl, an aryl carbonyl, an alkyl thiocarbonyl, an unsaturated alkyl thiocarbonyl, or an aryl thiocarbonyl, and R7a and R8a are the same or different and each is a saturated alkyl or an unsaturated alkyl, or, R7a and R8a, together with the nitrogen atom to which they are bonded, form a heterocycle containing 3 to about 7 atoms in the ring skeleton thereof; and E is H, a halogen, OR9, NHR9, or NR9R10, wherein R9 and R10 are the same or different and each is H, a protecting group, a saturated alkyl, an unsaturated alkyl, an alkylcarbonyl, an unsaturated alkyl carbonyl, an aryl carbonyl, an alkyl thiocarbonyl, an unsaturated alkyl thiocarbonyl, or an aryl thiocarbonyl. 9. The hydroxyl-protected alcohol of claim 1, wherein R is of the formula: wherein n is an integer from 0 to about 300; X is O, S or Se; R5 is H or a protecting group; R6 is H, a protecting group or a solid support; B is a labeling group, a saturated alkyl, an unsaturated alkyl, a cycloalkyl, an aryl, a heteroaryl with 5 to about 10 atoms, including at least one heteroatom selected from the group consisting of O, N, S, an oxide of N, and an oxide of S in the ring skeleton thereof, a heterocycloalkyl with 3 to about 10 atoms, including at least one heteroatom selected from the group consisting of O, N, S, an oxide of N, and an oxide of S in the ring skeleton thereof, a saturated alkyl with an aryl substituent, an unsaturated alkyl with an aryl substituent, an amino, an alkylamino, a dialkylamino, a purinyl, a pyrimidinyl, adeninyl, guaninyl, cytosinyl, uracilyl, or thyminyl, wherein B is unsubstituted or substituted with one or more substituents, which are the same or different, selected from the group consisting of a nucleobase protecting group R7, OR7, NHR7, NR7R8, N═CH--NR7aR8a N═C(alkyl)-NR7aR8aCN, NO1, N3, and a halogens wherein R7 and R8 are the same or different and each is H, a saturated alkyl, an unsaturated alkyl, an alkylcarbonyl, an unsaturated alkyl carbonyl, an aryl carbonyl, an alkyl thiocarbonyl, an unsaturated alkyl thiocarbonyl, or an aryl thiocarbonyl, and R7a and R8a are the same or different and each is a saturated alkyl or an unsaturated alkyl or, R7a and R8a together with the nitrogen atom to which they are bonded, form a heterocycle containing 3 to about 7 atoms in the ring skeleton thereof; and E is H, a halogen, OR9, NHR9, or NR9R10, wherein R9 and R10 are the same or different and each is H, a protecting group, a saturated alkyl, an unsaturated alkyl alkylcarbonyl, an unsaturated alkyl carbonyl, an aryl carbonyl, an alkyl thiocarbonyl, an unsaturated alkyl thiocarbonyl, or an aryl thiocarbonyl. 10. The hydroxyl-protected alcohol of claim 8, wherein B is selected from the group consisting of a purinyl, a pyrimidinyl, adeninyl, guaninyl, cytosinyl, uracilyl, and thyminyl. 11. A method of deprotecting a hydroxyl-protected alcohol, the method comprising heating the compound of claim 1 at a temperature effective to cleave thermally the Pg protecting Pg group therefrom, so as to deprotect and form the corresponding alcohol R--OH. 12. A method of producing an oligonucleotide, the method comprising: (a) reacting a nucleophile of the formula R6a--O--Q1--OH with an electrophile of the formula Pg--O--Q--O--P(Lg)--O--R5a to produce an adduct of the formula: (b) reacting the adduct obtained in step (a) with a reagent selected from the group consisting of oxidizing agents, sulfurizing agents, and selenizing agents to produce a hydroxyl-protected oligonucleotide of the formula: (c) heating the hydroxyl-protected oligonucleotide obtained in step (b) at a temperature effective to cleave Pg to produce a nucleophile; (d) optionally repeating steps (a)-(c) to produce an oligomer of the formula: (e) optionally removing R5a by deprotection; and (f) optionally removing R6a; wherein: Pg is a hydroxyl-protecting group of the formula: wherein: Y is R1, OR1, or NR1R1a; Z is O, NR2 or CR2R2a; W is CO; R1, R1a, R2, R2a, R3, R3a, R4 and R4a are the same or different and each is H, a saturated alkyl, an unsaturated alkyl, an aryl, a saturated alkyl with an aryl substituent, or an unsaturated alkyl with an aryl substituent, wherein: any of the alkyl-containing groups for R1, R1a, R2, R2a, R3, R3a, R4 or R4a is unsubstituted or substituted with one or more substituents, which are the same or different, and selected from the group consisting of a halogen, a saturated alkyl, an unsaturated alkyl, a hydroxyl, an alkoxy, an aryloxy, an aralkoxy, an alkyl carboxylate, an unsaturated alkyl carboxylate, an aryl carboxylate, an amide, a sulfhydryl, an alkyl sulfide, an aryl sulfide, an alkyl sulfoxide, an aryl sulfoxide, an alkyl sulfonyl, an aryl sulfonyl, an alkylcarbonyl, an unsaturated alkyl carbonyl, an aryl carbonyl, an alkyl thiocarbonyl, an unsaturated alkyl thiocarbonyl, an aryl thiocarbonyl, a cyano, and a nitro; any of the aryl-containing groups for R1, R1a, R2, R2a, R3, R3a, R4 or R4a is unsubstituted or substituted with one or more substituents, which are the same or different, and selected from the group consisting of a halogen, a saturated alkyl, an unsaturated alkyl, a hydroxyl, an alkoxy, an aryloxy, an aralkoxy, an alkyl carboxylate, an unsaturated alkyl carboxylate, an aryl carboxylate, an amide, a sulfhydryl, an alkyl sulfide, an aryl sulfide, an alkyl sulfoxide, an aryl sulfoxide, an alkylsulfonyl, an arylsulfonyl, an alkylcarbonyl, an unsaturated alkyl carbonyl, an aryl carbonyl, an alkyl thiocarbonyl, an unsaturated alkyl thiocarbonyl, an aryl thiocarbonyl, a cyano, a nitro, an amino, an alkylamino and a dialkylamino; and optionally, R1 or R1a is attached to a solid support; a, b, c, d, e and f are the same or different and each is H, a halogen, a saturated alkyl, an unsaturated alkyl, a hydroxyl, an alkoxy, an aryloxy, an aralkoxy, a cyano, a nitro, a sulfhydryl, an alkyl sulfide, an aryl sulfide, an alkyl sulfoxide, an aryl sulfoxide, an alkylsulfonyl, an arylsulfonyl, an alkylcarbonyl, an unsaturated alkyl carbonyl, an aryl carbonyl, an alkyl thiocarbonyl, an unsaturated alkyl thiocarbonyl, an aryl thiocarbonyl, an alkyl carboxylate, an unsaturated alkyl carboxylate, an aryl carboxylate, an amide, an amino, an alkylamino or a dialkylamino; and R is a nucleosidyl group, an oligonucleotidyl group with 2 to about 300 nucleosides, or an oligomer with 2 to about 300 nucleosides; n is an integer from 1 to about 300; Lg is a leaving group; R5a is a protecting group; R6a is a protecting group or a solid support; Q and Q1 are the same or different and each is a linking substituent selected from the group consisting of nucleosidyl group, an oligonucleotidyl group with 2 to about 300 nucleosides, and an oligomer with 2 to about 300 nucleosides; X is O, S or Se; and, when n is greater than 1, each Q is independently selected. 13. The method of claim 12, wherein Z is NR2. 14. The method of claim 12, wherein R2 is H or a saturated alkyl. 15. The method of claim 12, wherein Y is R1, and R1 is a saturated alkyl or aryl. 16. The method of claim 12, wherein R3 and R3a are H. 17. The method of claim 12, wherein R4 and R4a are H, or one of R4 and R4a are H and the other is aryl. 18. The method of claim 12, wherein Pg is selected from the group consisting of: 19. The method of claim 12, wherein R is of the formula: wherein: Q is a linking substituent selected from the group consisting of nucleosidyl group, an oligonucleotidyl group with 2 to about 300 nucleosides, and an oligomer with 2 to about 300 nucleosides; X is O, S or Se; R5 is H or a protecting group; R6 is H, a protecting group or a solid support; B is a labeling group, a saturated alkyl, an unsaturated alkyl, a cycloalkyl, an aryl, a heteroaryl with 5 to about 10 atoms, including at least one heteroatom selected from the group consisting of O, N, S, an oxide of N, and an oxide of S in the ring skeleton thereof, a heterocycloalkyl with 3 to about 10 atoms, including at least one heteroatom selected from the group consisting of O, N, S, an oxide of N, and an oxide of S in the ring skeleton thereof, a saturated alkyl with an aryl substituent, an unsaturated alkyl with an aryl substituent, an amino, an alkylamino, a dialkylamino, a purinyl, a pyrimidinyl, adeninyl, guaninyl, cytosinyl, uracilyl, or thyminyl, wherein B is unsubstituted or substituted with one or more substituents, which are the same or different, selected from the group consisting of a nucleobase protecting group, R7, OR7, NHR7, NR7R8, N═CH--NR7aR8a, N═C(alkyl)-NR7aR8a, CN, NO2, N3, and a halogen, wherein R7 and R8 are the same or different and each is H, a saturated alkyl, an unsaturated alkyl, an alkylcarbonyl, an unsaturated alkyl carbonyl, an aryl carbonyl, an alkyl thiocarbonyl, an unsaturated alkyl thiocarbonyl, or an aryl thiocarbonyl, and R7a and R8a are the same or different and each is a saturated alkyl or an unsaturated alkyl, or, R7a and R8a, together with the nitrogen atom to which they are bonded, form a heterocycle containing 3 to about 7 atoms in the ring skeleton thereof, and E is H, a halogen, OR9, NHR9, or NR9R10, wherein R9 and R10 are the same or different and each is H, a protecting group, a saturated alkyl, an unsaturated alkyl, an alkylcarbonyl, an unsaturated alkyl carbonyl, an aryl carbonyl, an alkyl thiocarbonyl, an unsaturated alkyl thiocarbonyl, or an aryl thiocarbonyl. 20. The method of claim 12, wherein R is of the formula: wherein n is an integer from 0 to about 300 X is O, S or Se; R5 is H or a protecting group; R6 is H, a protecting group or a solid support; B is a labeling group, a saturated alkyl, an unsaturated alkyl, a cycloalkyl, an aryl, a heteroaryl with 5 to about 10 atoms, including at least one heteroatom selected from the group consisting of O, N, S, an oxide of N, and an oxide of S in the ring skeleton thereof, a heterocycloalkyl with 3 to about 10 atoms, including at least one heteroatom selected from the group consisting of O, N, S, an oxide of N, and an oxide of S in the ring skeleton thereof, a saturated alkyl with an aryl substituent, an unsaturated alkyl with an aryl substituent, an amino, an alkylamino, a dialkylamino, a purinyl, a pyrimidinyl, adeninyl, guaninyl, cytosinyl, uracilyl, or thyminyl, wherein B is unsubstituted or substituted with one or more substituents, which are the same or different, selected from the group consisting of a nucleobase protecting group, R7, OR7, NHR7, NR7R8, N═CH--NR7aR8a, N═C(alkyl)-NR7aR8aa, CN, NO2, N3, and a halogen, wherein R7 and R8 are the same or different and each is H, a saturated alkyl, an unsaturated alkyl, an alkylcarbonyl, an unsaturated alkyl carbonyl, an aryl carbonyl, an alkyl thiocarbonyl, an unsaturated alkyl thiocarbonyl, or an aryl thiocarbonyl, and R7a and R8a are the same or different and each is a saturated alkyl or an unsaturated alkyl, or, R7a and R8a, together with the nitrogen atom to which they are bonded, form a heterocycle containing 3 to about 7 atoms in the ring skeleton thereof, and E is H, a halogen, OR9, NHR9, or NR9R10, wherein R9 and R10 are the same or different and each is H, a protecting group, a saturated alkyl, an unsaturated alkyl, an alkylcarbonyl, an unsaturated alkyl carbonyl, an aryl carbonyl, an alkyl thiocarbonyl, an unsaturated alkyl thiocarbonyl, or an aryl thiocarbonyl. 21. The method of claim 19, wherein B is selected from the group consisting of a purinyl, a pyrimidinyl, adeninyl, guaninyl, cytosinyl, uracilyl, and thyminyl. 22. The method of claim 20, wherein B is selected from the group consisting of a purinyl, a pyrimidinyl, adeninyl, guaninyl, cytosinyl, uracilyl, and thyminyl. 23. The method of claim 21, wherein B is selected from the group consisting of unsubstituted adeninyl, unsubstituted or substituted guaninyl, unsubstituted or substituted cytosinyl, and unsubstituted or substituted thyminyl. 24. The method of claim 22, wherein B is selected from the group consisting of unsubstituted adeninyl, unsubstituted or substituted guaninyl, unsubstituted or substituted cytosinyl, and unsubstituted or substituted thyminyl. 25. The hydroxyl-protected alcohol of claim 10, wherein B is selected from the group consisting of unsubstituted adeninyl, unsubstituted or substituted guaninyl, unsubstituted or substituted cytosinyl, and unsubstituted or substituted thyminyl. 26. The process of claim 12 further comprising wherein, in step (f) of said process, the oligonucleotidyl group, the polynucleotidyl group, or the nucleoside-containing oligomeric group is cleaved from the solid support R6a.