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A general method for the synthesis of C-glycosides of nojirimycin

journal contribution
posted on 2023-06-07, 20:04 authored by Thomas Fuchss, Hansjorg Streicher, Richard R Schmidt
Methyl 2,3,4,6-tetra-O-acetyl-N-(benzyloxycarbonyl)nojirimycin (3) can be readily transformed into the corresponding azaglycal 6 or fluoride 7, which are versatile glycosyl/piperidinosyl donors. Reaction of 7 with allyltrimethylsilane, propinyltrimethylsilane, trimethylsilyl cyanide, and trimethylsilyl enol ether as carbon nucleophiles, afforded, in the presence of BF3 . OEt2 as catalyst, the corresponding C-glycosides 8-10 and 12-14 in good yields. The anomeric configurations of the C-glycosides are ascertained with the help of ROESY-NMR data.

History

Publication status

  • Published

Journal

LIEBIGS ANNALEN-RECUEIL

ISSN

0947-3440

Issue

7

Page range

1315-1321

Department affiliated with

  • Chemistry Publications

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2012-02-06

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