A CONVENIENT PROCEDURE FOR THE SYNTHESIS OF 2,3,4,6-TETRA-O-BENZYL-D-GLUCONOLACTAM AND D-NOJIRILACTAM

被引：43

作者：

HOOS, R ^{[1
]}

NAUGHTON, AB ^{[1
]}

VASELLA, A ^{[1
]}

机构：

[1] UNIV ZURICH,INST ORGAN CHEM,CH-8057 ZURICH,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1993年 / 76卷 / 04期

关键词：

D O I：

10.1002/hlca.19930760435

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Swern oxidation of 2,3,4,6-tetra-O-benzyl-D-glucose (1) followed by ammonolysis gave the crystalline amide 3 which was oxidized (DMSO/pyridine . SO3) to yield the oxo-amide 4 and the hydroxy-lactams 5 and 6. Cyclization of 4 to the very slowly equilibrating 5 and 6 was completed by treatment with AcOH in CHCl3. The configuration of the hydroxy-lactams was assigned on the basis of NOEs. Reduction (Et3SiH/BF3 . Et2O) of the hydroxy-lactams either individually or as a mixture led to 2,3,4,6-tetra-O-benzyl-D-gluconolactam (7). The procedure, based upon modifications of a patent, does not require chromatography; the overall yield of 7 from 1 is 43%. Hydrogenolysis of 7 gave D-nojirilactam (8); benzylation led to the known pentabenzyl-D-nojirilactam (9) and to the unsaturated lactam 10.

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页码：1802 / 1807

页数：6

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