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Syntheses of New Amino and Aziridino Sugar Derivatives of Potential Biochemical Interest
Author(s) -
Latif Farzana,
Malik Abdul,
Voelter Wolfgang
Publication year - 1987
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198719870815
Subject(s) - chemistry , isomerization , sugar , trimethylsilyl azide , azide , stereochemistry , organic chemistry , medicinal chemistry , catalysis
Efficient one‐pot syntheses of some amino and aziridino sugars of potential biochemical interest are developed by way of a CN coupling reaction between suitably protected sugars and esters of p ‐aminobenzoic acid. The free amino function of the latter are utilized to cause S N 2 displacement of the triflyl group in the sugar triflates 1–3 providing a new class of amino sugars ( 4–8 ). The reactions of 4 and 5 with Et 2 OBF 3 in trimethylsilyl azide afford a new type of aziridino sugars ( 9–10 ) through a novel isomerization of an α‐iminooxirane into an α‐hydroxyepimine. The reaction pathway also provides benzyl 4‐[4‐( tert ‐butyloxycarbonyl)phenylamino]‐4‐deoxy‐β‐ L ‐lyxopyranoside ( 11 ) and its α‐ D ‐isomer 12 . The conformation of compounds 4–11 are supported by 1 H‐ and 13 C‐NMR spectroscopy.