Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters

Carvalho, Ivone, Scheuerl, Shona L., Kartha, K. P. Ravindranathan and Field, Robert A. ORCID: https://orcid.org/0000-0001-8574-0275 (2003) Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters. Carbohydrate Research, 338 (10). pp. 1039-1043. ISSN 0008-6215

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Abstract

Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding β-glycosides in good yields (64 and 62%, respectively). Direct coupling of the commercially available Fmoc-Ser-OH and Fmoc-Thr-OH carboxylic acids under similar conditions gave the corresponding β-glycosides, possessing free carboxyl groups, in moderate yields (50 and 40%, respectively).

Item Type:	Article
Additional Information:	Funding Information: These studies were supported by the MRC and the Weston Foundation. Support in the form of a research leave fellowship from FAPESP is gratefully acknowledged (IC). We thank Julia Bilke for performing some preliminary glycosylation experiments. We are indebted to the EPSRC Mass Spectrometry Service Centre, Swansea for invaluable support.
Uncontrolled Keywords:	benzyl ester,free carboxylic acid,glycosylation,mercuric bromide,serine,threonine,analytical chemistry,biochemistry,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1602
Faculty \ School:	Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
Related URLs:	http://www.scopus.com/inward/record.url?...
Depositing User:	LivePure Connector
Date Deposited:	10 Sep 2024 12:30
Last Modified:	25 Sep 2024 18:08
URI:	https://ueaeprints.uea.ac.uk/id/eprint/96658
DOI:	10.1016/S0008-6215(03)00071-5

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