Alkylating agents from sugars: Synthesis of chlorambucil derivatives carried by chiral glycosyl glycerols derived from  D ‐Glucosamine | Zendy

IglesiasGuerra Fernando | Zendy; Candela José I. | Zendy; Blanco Eugenia | Zendy; Alcudia Felipe | Zendy; VegaPérez José M. | Zendy

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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.

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