[미국특허]
Preparation of phosphorothioate oligomers
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07H-021/00
C07H-001/02
C07F-096/584
출원번호
US-0948152
(1997-10-09)
발명자
/ 주소
Just George,CAX
Xin Zhili,CAX
Marsault Eric,CAX
Jin Yi,CAX
출원인 / 주소
McGill University, CAX
대리인 / 주소
Woodcock Washburn Kurtz MacKiewicz & Norris, LLP
인용정보
피인용 횟수 :
23인용 특허 :
8
초록
Methods and intermediates for the preparation of oligomers containing diastereomerically enriched phosphorothioate linkages are disclosed.
대표청구항▼
[ What is claimed is:] [1.] An azaphospholane of Formula VIb: [ STR 95 ] wherein: Y is X or W wherein X is halogen, dialkylamino, imidazole, triazole or substituted phenoxy wherein said substituents are electron withdrawing, and W has the formula: [ STR 96 ] wherein: Q is independently O or S;R.sup.
[ What is claimed is:] [1.] An azaphospholane of Formula VIb: [ STR 95 ] wherein: Y is X or W wherein X is halogen, dialkylamino, imidazole, triazole or substituted phenoxy wherein said substituents are electron withdrawing, and W has the formula: [ STR 96 ] wherein: Q is independently O or S;R.sup.1 is a hydroxyl protecting group;R.sup.2 is a chiral auxiliary of formula --C (R.sup.8)R.sup.3 --C(R.sup.16)R.sup.5 --CHR.sup.6 --NHR.sup.7 ;R.sup.3 is hydrogen, alkyl, cyanomethyl, monohalomethyl, dihalomethyl, trihalomethyl, --CH.sub.2 Si(R.sup.4).sub.3, or --CH.sub.2 --SO.sub.k R.sup.4 where k is 0, 1 or 2;R.sup.4 is independently alkyl, aryl, aralkyl or alkaryl having up to 15 carbon atoms;R.sup.5 is H, --CN, --Si(R.sup.4).sub.3, SO.sub.k R.sup.4 or halogen;or R.sup.8 and R.sup.16 are each H, and R.sup.3 and R.sup.5, together, form one of the structures [ STR 97 ] wherein: R.sup.10 and R.sup.11 are H, alkyl having from 1 to about 10 carbons, --CH.sub.2 C(.dbd.O)OR.sup.22, --CH.sub.2 CN, --CH.sub.2 Si(CH.sub.3).sub.3, or o- or p-C.sub.6 H.sub.4 --R.sup.21 ;R.sup.21 is hydrogen, --O--C(.dbd.O)CH.sub.3, alkoxy having from 1 to about 10 carbons, --NO.sub.2, or --N(R.sup.22).sub.2 ;R.sup.22 is independently H or alkyl having from one to about 10 carbon atoms;p is 1 or 2;Z.sup.1 and Z.sup.2 are independently halogen, CN, --Si(CH.sub.3).sub.3, and --C(.dbd.O)OR.sup.22 ;R.sup.30 is hydrogen, --O--C(.dbd.O)CH.sub.3, alkoxy having from 1 to about 10 carbons, or --O--Si(R.sub.4).sub.3 ;R.sup.6 is H, alkyl or aralkyl having up to 15 carbon atoms;or R.sup.5 and R.sup.6, together with the atoms to which they are attached, form a 5 or 6 membered ring;R.sup.7 is alkyl or aralkyl having up to 15 carbon atoms;or R.sup.6 and R.sup.7, together, form one of the structures [ STR 98 ] wherein X, T, and Z are independently CH or NH; or Z and R.sup.5, together with the atoms to which they are attached, form a phenyl ring;R.sup.8 is H or methyl;R.sup.9 is a hydxoxyl protecting group or a solid support;R.sup.16 is H, alkyl or aralkyl having up to 15 carbon atoms;B is a nucleobase; andn is an integer from 0 to 50.
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Wojciech J. Stec PL; Lucyna A. Wozniak PL; Arkadiusz Chworos PL; Jaroslaw Pyzowski PL, Process for the synthesis of modified P-chiral nucleotide analogues.
Woolf, Tod M.; Kamens, Joanne; Salomon, William; Khvorova, Anastasia, RNA duplexes with single stranded phosphorothioate nucleotide regions for additional functionality.
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