NUCLEOSIDES .6. A NOVEL AND CONVENIENT SYNTHESIS OF PURINE S-CYCLONUCLEOSIDES VIA MITSUNOBU REACTION

被引：10

作者：

CHERN, JW ^{[1
]}

KUO, CC ^{[1
]}

CHANG, MJ ^{[1
]}

LIU, LT ^{[1
]}

机构：

[1] NATL DEF MED CTR,INST PHARM,TAIPEI,TAIWAN

来源：

NUCLEOSIDES & NUCLEOTIDES | 1993年 / 12卷 / 09期

关键词：

D O I：

10.1080/07328319308018564

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：

Two representative S-cyclonucleosides, 8,5'-anhydro-2', 3'-O-isopropylidene-8-mercaptoadenosine (3) and 8,2'-anhydro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-8-mercaptoguanosine (8), were prepared in good yields by dropwise addition of one equivalent each of triphenylphosphine and DEAD in DMF into a mixture of 2',3'-O-isopropylidene-8-mercaptoadenosine (2) or 3',5'-O-(tetra-iso-propyldisiloxane-1,3-diyl)-8-mercaptoguanosine (7), respectively, in DMF. Treatment of compound 2 with two equivalents each of triphenylphosphine and DEAD in DMF afforded N-[8,5'-anhydro-2',3'-0-isopropylidene-8-mercaptopurin-6-yl]triphenylphospha-lambda5-azene (4) in 87% yield.

引用

页码：941 / 949

页数：9

共 13 条

[1] SYNTHESIS OF N-ACYL, N-SULFONYL, AND "N-PHOSPHINYLPHOSPHA-LAMBDA-5-AZENES BY A REDOX-CONDENSATION REACTION USING AMIDES, TRIPHENYLPHOSPHINE, AND DIETHYL AZODICARBOXYLATE [J].