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A Convenient Procedure for he Synthesis o 2,3,4,6-Tetra-O-benzyl-D-gluconolactam and D-Nojirilactam

✍ Scribed by Roland Hoos; Andrew B. Naughton; Andrea Vasella

Book ID
102254292
Publisher
John Wiley and Sons
Year
1993
Tongue
German
Weight
445 KB
Volume
76
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Swern oxidation of 2,3,4,5‐tetra‐O‐benzyl‐D‐glucose (1) followed by ammonolysis gave the crystalline amide 3 which was oxidized (DMSO/pyridine · SO~3~) 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 CHCl~3~. The configuration of the hydroxy‐lactams was assigned on the basis of NOEs. Reduction (Et~3~SiH/BF~3~ · Et~2~O) 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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