O-(1-PHENYL-1H-TETRAZOL-5-YL) GLYCOSIDES - ALTERNATIVE SYNTHESIS AND TRANSFORMATION INTO GLYCOSYL FLUORIDES

被引：25

作者：

PALME, M ^{[1
]}

VASELLA, A ^{[1
]}

机构：

[1] ETH ZENTRUM,ORGAN CHEM LAB,CH-8092 ZURICH,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1995年 / 78卷 / 04期

关键词：

D O I：

10.1002/hlca.19950780418

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A number of new glycosyl donors, O-(1-phenyl-1H-tetrazol-5-yl) glycosides, are prepared from the corresponding hemiacetals, commercially available 5-chloro-1-phenyl-1H-tetrazole (2), and tetrabutylammonium fluoride (Bu(4)NF) in either THF or DMF. The mild reaction conditions are compatible with a variety of protecting groups. The glycosyl donors are treated with hydrogen fluoride-pyridine complex (HF . py) to rapidly provide glycosyl fluorides in good-to-excellent yields, apparently by a (single or double) S(N)2 mechanism as studied by both H-1- and F-19-NMR spectroscopy. Under acidic conditions, glycosyl fluorides equilibrate partially or completely, equilibration requiring a large excess of HF . py.

引用

页码：959 / 969

页数：11

共 52 条

[1] SYNTHETIC STUDIES BY THE USE OF FLUORINATED INTERMEDIATES .1. A NOVEL PROCEDURE FOR C-GLYCOSYLATION INVOLVING LEWIS ACID-CATALYZED COUPLING-REACTIONS OF GLYCOSYL FLUORIDES WITH ENOL TRIMETHYLSILYL ETHERS [J].