SONOCHEMICAL AND TRIETHYLBORANE-INDUCED TIN DEUTERIDE REDUCTION FOR THE HIGHLY STEREOSELECTIVE SYNTHESIS OF (2'R)-[2'-H-2]-2'-DEOXYRIBONUCLEOSIDES FROM 2'-FUNCTIONALIZED RIBONUCLEOSIDES

被引：22

作者：

KAWASHIMA, E

AOYAMA, Y

SEKINE, T

NAKAMURA, E

KAINOSHO, M

KYOGOKU, Y

ISHIDO, Y

机构：

[1] TOKYO COLL PHARM,FAC PHARM,PHARMACEUT CHEM LAB,1432-1 HORINOUCHI,HACHIOJI,TOKYO 19203,JAPAN

[2] TOKYO INST TECHNOL,FAC SCI,DEPT CHEM,MEGURO KU,TOKYO 152,JAPAN

[3] TOKYO METROPOLITAN UNIV,FAC SCI,DEPT CHEM,HACHIOJI,TOKYO 19203,JAPAN

[4] OSAKA UNIV,INST PROT RES,SUITA,OSAKA 565,JAPAN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 08期

关键词：

D O I：

10.1016/S0040-4039(00)91784-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(Bu3SnH)-H-2-reduction of a 2'-bromo-2'-deoxyuridine benzoate under high-intensity ultrasound irradiation at -71-degrees-C resulted in highly efficient deuterium incorporation to afford a 96:4 mixture of (2'R)- and (2'S)-[2,-H-2]-2'-deoxyuridine. The use of both Et3B, as an alternative radical generator, and 2'-bromo-2'-deoxy-3',5'-O-TPDS-ribonucleosides made it feasible to perform the reaction in a preparative scale in addition to an excellent stereoselectivity (>99:1).

引用

收藏

页码：1317 / 1320

页数：4

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