An Improved Method for the Synthesis of 3.6-Di-O-Methyl-D-Glucose: Preparation of the Neo-Glycoprotein Containing 3,6-Di-O-Methyl-β-D-Glucopyranosyl-Groups
Titel:
An Improved Method for the Synthesis of 3.6-Di-O-Methyl-D-Glucose: Preparation of the Neo-Glycoprotein Containing 3,6-Di-O-Methyl-β-D-Glucopyranosyl-Groups
Auteur:
Sen, Asish K. Sarkar, Kalyan K. Banerji, Nilima
Verschenen in:
Journal of carbohydrate chemistry
Paginering:
Jaargang 7 (1988) nr. 3 pagina's 645-654
Jaar:
1988-09-01
Inhoud:
3,6-Di-O-methyl-D-glucose, the non-reducing terminal sugar of the phenolic glycolipid-I, elaborated by Mycobacterium leprae, has been synthesized by a simple procedure and in high yield. 3-O-Methyl-D-glucose was converted to the corresponding benzyl glycoside and then tosylated to give benzyl 3-O-methyl-6-O-tosyl-β-D-glucopyranoside. Displacement of tosyl group with sodium methoxide followed by debenzylation afforded 3,6-di-O-methyl-D-glucose in high yield. Condensation of the acetobromo derivative of 3,6-di-O-methyl-D-glucose with 8-ethoxycarbonyloctanol gave 8-ethoxycarbonyloctyl 2,4-di-O-acety 1-3, 6-di-O-methy 1-β-D-glucopyranoside. This was then deacetylated, converted to hydrazide, and finally coupled to bovine serum albumin via the acyl azide intermediate. The neo-glycoprotein containing the 3,6-di-O-methyl-β-D-glucopyranosyl group is useful for serodiagnosis of leprosy.