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Alkylating agents from sugars: Synthesis of chlorambucil derivatives carried by chiral glycosyl glycerols derived from D ‐Glucosamine
Author(s) -
IglesiasGuerra Fernando,
Candela José I.,
Blanco Eugenia,
Alcudia Felipe,
VegaPérez José M.
Publication year - 2002
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10061
Subject(s) - chemistry , glycosyl , chlorambucil , hydrolysis , moiety , glucosamine , stereochemistry , amide , yield (engineering) , organic chemistry , medicine , materials science , surgery , chemotherapy , metallurgy , cyclophosphamide
Chlorambucilamide derivatives involving chiral glycosyl glycerols derived from D ‐glucosamine were synthesized in good yield by coupling the chlorambucil moiety to the amino group of ω‐amino‐(ω‐1)‐hydroxyalkyl 2‐acylamino‐4,6‐ O ‐benzylidene‐2‐deoxy‐β‐ D ‐glucopyranosides, and subsequent hydrolysis of the benzylidene group. The starting material was easily available from 2‐acetamido‐2‐deoxy‐ D ‐glucose. The bonding of 2,3,4,6‐tetra‐ O ‐pivaloyl‐β‐ D ‐galactopyranosylamine to chlorambucil by formation of an amide function is also described. Chirality Chirality 14:199–203, 2002. © 2002 Wiley‐Liss, Inc.