REGIOSELECTIVE 2'/3'-O-ALLYLATION OF PYRIMIDINE RIBONUCLEOSIDES USING PHASE-TRANSFER CATALYSIS

被引:11
作者
GOPALAKRISHNAN, V [1 ]
KUMAR, V [1 ]
GANESH, KN [1 ]
机构
[1] NATL CHEM LAB,DIV ORGAN CHEM,BIOORGAN CHEM UNIT,POONA 411008,MAHARASHTRA,INDIA
来源
NUCLEOSIDES & NUCLEOTIDES | 1992年 / 11卷 / 06期
关键词
D O I
10.1080/07328319208018341
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A short and convenient procedure for regiospecific O-allylation of uridine is reported by employing dibutyltin oxide as a mild base in conjunction with a phase transfer catalyst tetrabutylammonium bromide. The resulting isomeric 2'/3'-O-allyl uridines were separated after conversion into their corresponding 5'-O-DMT derivatives. The 2'-O-allyluridine 3 was then transformed into 2'-O-allylcytidine 7 and both were individually converted into the corresponding beta-cyanoethyl phosphoramidite monomers (9 and 10) and a phosphodiester monomer 11, required for oligonucleotide assembly. The utility of 11 is demonstrated by synthesis and characterization of a 2'-O-allyl ribodinucleotide UpU.
引用
收藏
页码:1263 / 1273
页数:11
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