Synthesis of a thio analogue of n-propyl kojibioside, a potential glucosidase inhibitor

✍ Scribed by John S. Andrews; B. Mario Pinto

• Book ID: 102990468
• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 607 KB
• Volume: 270
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(95)00014-k

✦ Synopsis

The disaccharide a-D-Glcp-(1-S-2)-fl-D-Glcp-(1-OPr) 1, a thio analogue of a-D-Glcp-( 12)-a-D-Glcp-(1-OPr)(n-propyl kojibioside) in which the inter-glycosidic oxygen atom is replaced by sulfur, has been synthesized for evaluation as a potential glucosidase inhibitor. Glycosylation of the 2-thiol glucopyranosyl acceptor 4 with the trichloroacetimidate of 2,3,4,6-tetra-O-benzyl-a-D-glucopyranose 5 gave the a-linked disaccharide 6 stereoselectively. Deprotection was performed by hydrogenolysis in the presence of Pd/C to give 1 as the /3-n-propyl glycoside. Glycosylation of the thiol 4 with the trichloroacetimidate of 2,3,4,6-tetra-O-acetyl-a-D-glucopyranose 8 gave a 1:2.3 mixture of the a and /3 disaceharides (9 and 10); evidence is presented for the occurrence of the orthoester 11, as an intermediate in the formation of the /3-disaccharide.