Syntheses of derivatives of N-acetyl-D-lactosamine from D-lactal hexaacetate. Hexa-O-acetyl-2-deoxy-2-phthalimido-β-D-lactosyl chloride
- 1 January 1982
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 60 (1) , 63-67
- https://doi.org/10.1139/v82-011
Abstract
Two reaction routes are presented for the preparation of hexa-O-acetyl-2-deoxy-2-phthalimido-.beta.-D-lactosyl chloride (7) from lactal hexaacetate (1). One route involves, in the first stage, reaction of 1 with nitrosyl chloride and proceeds by way of benzyl 2-amino-2-deoxy-2-.alpha.-D-lactoside (4) as an intermediate. The other route, which is considered more efficient, involves reaction of 1 with ceric ammonium nitrate and sodium azide and involves the .beta.-anomer of 4 as an intermediate. The preparation of 7 is of interest as a reagent for the preparation of 2-amino-2-deoxy-.beta.-D-lactosides. The procedures offer routes for the preparation of D-lactosamine.This publication has 5 references indexed in Scilit:
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