5-Amino-5-deoxy-1-thioglucopyranosides - synthesis of thioglycoside derivatives of nojirimycin

Article abstract of DOI:10.1080/07328300008544110

N-Benzyloxycarbonyl-protected 5-amino-5-deoxyglucofuranose derivative 1 could be readily transformed into 6-O, N-carbonylidene nojirimycin 3 which afforded the corresponding piperidinosyl trichloroacetimidate 6. This compound turned out to be a versatile piperidinosyl donor. Reaction with various mercaptans as acceptors in the presence of TMSOTf as catalyst gave 5-aza-1-thioglucopyranosides 7a-c, 9, and 13 which were successfully deprotected.

Full text of DOI:10.1080/07328300008544110

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5-Amino-5-Deoxy-1-
Thioglucopyranosides-Synthesis
of Thioglycoside Derivatives of
Nojirimycin
Thomas Fuchss & Richard R. Schmidt
a Fakultät Chemie, Universität Konstanz, Fach M 725,
D-78457 Konstanz, Germany
b Fakultät Chemie, Universität Konstanz, Fach M 725,
D-78457 Konstanz, Germany
Published online: 27 Feb 2008.
To cite this article: Thomas Fuchss & Richard R. Schmidt (2000): 5-Amino-5-Deoxy-1-
Thioglucopyranosides-Synthesis of Thioglycoside Derivatives of Nojirimycin, Journal of
Carbohydrate Chemistry, 19:6, 677-691
To link to this article: http://dx.doi.org/10.1080/07328300008544110
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