TRI-O-ACYL 2-DEOXY-D-RIBOFURANOSE - AN EFFECTIVE ENZYME-ASSISTED ONE-POT SYNTHESIS FROM 2-DEOXY-D-RIBOSE AND TRANSFORMATION INTO 2'-DEOXYNUCLEOSIDES

被引：40

作者：

PRASAD, AK ^{[1
]}

SORENSEN, MD ^{[1
]}

PARMER, VS ^{[1
]}

WENGEL, J ^{[1
]}

机构：

[1] ODENSE UNIV,DEPT CHEM,DK-5230 ODENSE M,DENMARK

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 34期

关键词：

D O I：

10.1016/0040-4039(95)01216-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective lipase-catalyzed (Novozym 435(R) from Candida antartica) acylations of unprotected 2-deoxy-D-ribose and D-ribose, by use of propionic anhydride, afforded the novel 5-O-monoacylated derivatives 1 and 4, respectively. Subsequent addition of acetic anhydride and pyridine into the reaction mixtures gave the corresponding per-O-acylated pentofuranoses 2 and 5 in almost quantitative overall yields from the unprotected carbohydrates. The versatility of compound 2 as an universal synthon for synthesis of anomeric mixtures of 2'-deoxynucleosides is demonstrated.

引用

页码：6163 / 6166

页数：4

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