Tris(trimethylsilyl)[H-2]silane-triethylborane system producing the highly diastereoselective deuteration (> 99:1) of 2'-bromo-2'-deoxy- and 2'-O-phenoxythiocarbonylribonucleosides at 0 degrees C

被引：11

作者：

Kawashima, E ^{[1
]}

Uchida, S ^{[1
]}

Miyahara, M ^{[1
]}

Ishido, Y ^{[1
]}

机构：

[1] TOKYO UNIV PHARM & LIFE SCI,SCH PHARM,LAB PHARMACEUT CHEM,HACHIOJI,TOKYO 19203,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 42期

关键词：

D O I：

10.1016/S0040-4039(97)01722-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reductive protylation and deuteration reactions using (Me3Si)(3)SiH- and (Me3Si)(3)(SiH)-H-2-Et3B systems were investigated in view of the differences in bond energy and bond length between the Si-H of (Me3Si)(3)SiH and the Sn-H of Bu3SnH. Higher diastereoselectivity was obtained in comparison with the reactions using the Bu3SnH - and (Bu3SnH)-H-2-Et3B systems; the (Me3Si)(3)SiH system gave remarkable diastereoselectivity of 98.7% at 0 degrees C, whereas the other system required temperatures below -70 degrees C. (C) 1997 Elsevier Science Ltd.

引用

页码：7369 / 7372

页数：4

共 5 条

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