1H-tetrazole as catalyst in phosphomorpholidate coupling reactions: Efficient synthesis of GDP-fucose, GDP-mannose, and UDP-galactose

被引：170

作者：

Wittmann, V ^{[1
]}

Wong, CH ^{[1
]}

机构：

[1] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 07期

关键词：

D O I：

10.1021/jo9620066

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved procedure is described for the efficient and high-yield (76-91%) synthesis of nucleoside diphosphate sugars from the readily available nucleoside 5'-monophosphomorpholidate and sugar l-phosphate in the presence of VI-tetrazole, Comparative kinetic investigations by means of P-31 NMR spectroscopy with different additives (1,a,4-triazole, acetic acid, N-hydroxysuccinimide, 4-(dimethylamino)pyridine hydrochloride, perchloric acid) and mass spectrometric analysis suggest that tetrazole acts as an acid and as a nucleophilic catalyst in the pyrophosphate bond formation.

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页码：2144 / 2147

页数：4

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