Synthesis of 4‐O‐(3,4,6‐tri‐O‐acetyl‐2‐deoxy‐2‐phthalimido‐β‐D‐glucopyranosyl)‐1,6‐anhydro‐3‐O‐(4‐methoxybenzoyl)‐β‐ D‐mannopyranose: A versatile intermediate for the preparation of N,N‐diacetylchitobiose derivatives

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Abstract
4‐O‐Acetyl‐1,6‐anhydro‐3‐O‐(4‐methoxybenzoyl)‐β‐D ‐mannopyranose was converted in two steps into 4‐O‐acetyl‐1,6‐anhydro‐2‐deoxy‐2‐phthalimido‐β‐D‐glucopyranose. Trimethylsilyl tri‐fluoromethanesulphonate‐catalysed coupling of 1,6‐anhydro‐2,3‐O‐(4‐methoxybenzylidene)‐β‐D‐mannopyranose with 1,3,4,6‐tetra‐O‐acetyl‐2‐deoxy‐2‐phthalimido‐β‐D‐glucopyranose, followed by treatment with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone, afforded the title compound. After triflation, the disaccharide thus obtained was treated with lithium azide or potassium phthalimide to afford 4‐O‐(3,4,6‐tri‐O‐acetyl‐2‐deoxy‐2‐phthalimido‐β‐D‐ glucopyranosyl)‐1,6‐anhydro‐2‐azido‐3‐O‐(4‐methoxy‐benzoyl)‐2‐deoxy ‐β‐D‐glucopyranose and 4‐O‐(3,4,6‐tri‐O‐acetyl‐2‐deoxy‐2‐phthalimido‐β‐D ‐glucopyranosyl) −1,6‐anhydro‐2‐deoxy‐3‐O‐(4‐methoxybenzoyl)‐2‐phthalimido‐β‐ D‐glucopyranose, respectively.

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