Synthesis of D-altritol nucleosides with a 3′-O-Tert-butyldimethylsilyl protecting group

被引：9

作者：

Abramov, M ^{[1
]}

Marchand, A ^{[1
]}

Calleja-Marchand, A ^{[1
]}

Herdewijn, P ^{[1
]}

机构：

[1] Katholieke Univ Leuven, Rega Inst Med Res, Med Chem Lab, B-3000 Louvain, Belgium

来源：

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2004年 / 23卷 / 1-2期

关键词：

D-altritol nucleosides; 3 '-O-tert-butyldimethylsilyl protecting group; 1,5 : 2,3-dianhydro-4,6-O-benzylidene-D-allitol;

D O I：

10.1081/NCN-120028338

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：

Four D-altritol nucleosides with a 3'-O-tert-butyldimethylsilyl protecting group are synthesized (base moieties are adenine, guanine, thymine and 5-methylcytosine). The nucleosides are obtained by ring opening reaction of 1,5:2,3-dianhydro-4,6-O-benzylidene-D-allitol. Optimal reaction circumstances (NaH, LiH, DBU, phase transfer, microwave irridation) for the introduction of the heterocycles are base-specific. For the introduction of the 3'-O-silyl protecting group, long reaction times and several equivalents of tert-butyldimethylsilyl chloride are needed.

引用

页码：439 / 455

页数：17

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