Journal article icon

Journal article

Intermediates for incorporation of tetrahydroxypipecolic acid analogues of alpha- and beta-D-mannopyranose into combinatorial libraries: unexpected nanomolar-range hexosaminidase inhibitors. Synthesis of alpha- and beta-homomannojirimycin

Abstract:

Homoazasugars have the distinction as a class of natural products in that most of them have been synthesised before they were isolated. Syntheses of α-1 and β-homomannojirimycin 2 rely on the stereoselective and chemoselective sodium cyanoborohydride reduction of a [2.2.2] bicyclic imino lactone (6) to give a single [2.2.2] bicyclic amino-lactone (7). Methanolysis of 7 under basic conditions is accompanied by efficient epimerisation of the first formed α-amino-ester (8) to the more stable β-a...

Expand abstract
Publication status:
Published

Actions


Access Document


Authors


Shilvock, JP More by this author
Winters, AL More by this author
Expand authors...
Journal:
TETRAHEDRON-ASYMMETRY
Volume:
9
Issue:
19
Pages:
3505-3516
Publication date:
1998-10-02
DOI:
ISSN:
0957-4166
URN:
uuid:2901b34b-35f7-425e-8aa0-23120b44331e
Source identifiers:
36681
Local pid:
pubs:36681
Language:
English

Terms of use


Metrics



If you are the owner of this record, you can report an update to it here: Report update to this record

TO TOP