Synthesis of benzoylated -D-glucosamine derivatives
Claudia Di Salvo
a , Karen A. Fox
a
, Jens Langhanki
b,†
, Paul V. Murphy
a, *
a School of Chemistry, National University of Ireland Galway, University Road, Galway,
Ireland.
b Institute of Organic Chemistry, University of Mainz, Duesbergweg 10–14, D55128 Mainz, Germany
The preparation of intermediates for synthesis of D-glucosamine (2-amino-2-deoxy-Dglucopyranose) derivatives is of interest. The synthesis of 1,3,4,6-tetra-O-acetyl-2-amino-2deoxy--D-glucopyranose hydrochloride, described originally by Bergmann and Zervas
1 in
1931, is often used to prepare glucosamine derivatives.
2,3 This includes preparation of
compounds for screening for medical applications where D-glucosamine is a core scaffold.
4
The analogous preparation of 2-amino-2-deoxy-1,3,4,6-tetra-O-benzoyl--D-glucopyranose
hydrochloride 4 and its acetamide derivative 5, is also of interest. For example, the use of
benzoates instead of acetate protecting groups in carbohydrate chemistry can lead to an
enhancement in the rate of anomerisation reactions,
5 and lead to increased yields from such
† Checker under the supervision of Prof. Dr. Till Opatz; e-mail: opatz@uni-mainz.de
* Corresponding author; e-mail: paul.v.murphy@nuigalway.ie