Potential HIV protease inhibitors: Preparation of di- N-alkylated 2-, 6-, and 2,6-aminodeoxy-derivatives of d-glucose by direct displacement and by a novel reductive-alkylation procedure

Glucose derivatives carrying branched lipophilic groups at the 2-, 6-, and 2,6-positions were required for biological testing as inhibitors of the protease produced by the human immunodeficiency virus. The synthesis of (N- benzyl-N- ethyl)-2-, 6- and 2,6-diaminodeoxy- d-glucose derivatives is descri...

Full description

Saved in:
Bibliographic Details
Published in:Carbohydrate research 1997-05, Vol.300 (2), p.109-117
Main Authors: Cai, Jiaqiang, Davison, Bruce E., Ganellin, C.Robin, Thaisrivongs, Suvit, Wibley, Keith S.
Format: Article
Language:English
Subjects:
( N-Benzyl- N-ethyl)-aminodeoxyglucose derivatives
Allyl [formula omitted]
formula omitted
Reductive alkylation
Sulphonate displacement
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Glucose derivatives carrying branched lipophilic groups at the 2-, 6-, and 2,6-positions were required for biological testing as inhibitors of the protease produced by the human immunodeficiency virus. The synthesis of (N- benzyl-N- ethyl)-2-, 6- and 2,6-diaminodeoxy- d-glucose derivatives is described. The 2- tert-amino group was introduced by a two-step reductive alkylation procedure. The novel tertiary aminosugar, 2,6-di-(N- benzyl-N- ethyl)amino-2,6-dideoxy- d-glucose , was made via direct substitution of the sulphonate group in allyl 2-acetamido-2-deoxy-6-O- tosyl- d-glucopyranoside with N- benzylethylamine . The syntheses of the title compounds ( 11), ( 15), and ( 23) are described.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(97)00039-6