Synthesis of 2, 2, 2-trichloroethyl 3, 6-di-O-benzyl-2-deoxy-2-phthalimido-β-d-glucopyranoside, and its reaction with glycosyl halides.
T Ogawa, S Nakabayashi, K Sasajima
Index: Ogawa, Tomoya; Nakabayashi, Satoru; Sasajima, Kikuo Carbohydrate Research, 1981 , vol. 95, p. 308 - 312
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Citation Number: 21
Abstract
Abstract 2, 2, 2-trichloroethyl 3, 6-di-O-benzyl-2-deoxy-2-phthalimido-β-d-glucopyranoside (9) was synthesized in 6 steps from the readily available 1, 3, 4, 6-tetra-O-acetyl-2-deoxy-2- phthalimido-β-d-glucopyranose in 25% overall yield by employing the stannyl method for the regioselective activation of hydroxyl groups. Dibenzyl ether 9 was then glycosylated with appropriate glycosyl donors to afford lactosamine and chitobiose derivatives in good yield.
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