D-ARBINOSE-BASED SYNTHESIS OF HOMO-C-d4T AND HOMO-C-THYMIDINE

被引：9

作者：

Doboszewski, Bogdan ^{[1
,2
]}

机构：

[1] Univ Fed Rural Pernambuco, Dept Quim, BR-52171900 Recife, PE, Brazil

[2] Univ Fed Pernambuco, Dept Antibiot, Recife, PE, Brazil

来源：

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2009年 / 28卷 / 10期

关键词：

D-arabinose; deoxygenation; C-glycoside; Grignard reagents; Mitsunobu coupling; C-nucleoside; stereoselectivity; NUCLEOSIDE ANALOGS; GLYCOSYLATION REACTIONS; STEREOSPECIFIC SYNTHESIS; D-ARABINOFURANOSYL; AMINO-ACIDS; GLYCOSIDES; DERIVATIVES; SUGAR; STEREOSELECTIVITY; CONFORMATION;

D O I：

10.1080/15257770903306518

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：

2,3,5-Tri-O-benzyl-D-arabinofuranosyl halides (chloride, bromide) were reacted with AllMgBr; MeMgBr, and VinMgBr to furnish anomeric mixtures of the C-glycosyl products. The factors that influenced the beta/alpha ratio are discussed. The alpha,beta-C-vinyl derivative was transformed into 1-deoxy-1-C-hydroxymethyl-beta- and -alpha-D-arabinofuranoses (2,5-anhydro-D-glucitol and -mannitol, ;respectively), separable after isopropylidenation step. 2,5-Anhydro-1,3-O-isopropylidene-D-glucitol was converted into 2,5-anhydro-6-O-triphenylmethyl-D-erythro-hex-3,4-enitol and 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol, which were coupled. with N-3-benzoylthymine under the Mitsunobu conditions to furnish two analogs of nucleosides with a -CH2- insert between sugar moieties and thymine. [GRAPHICS] .

引用

页码：875 / 901

页数：27

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