Shaban M A, Jeanloz R W
Carbohydr Res. 1976 Dec;52:103-14. doi: 10.1016/s0008-6215(00)85951-0.
Condensation of 4,6-di-O-acetyl-2,3-O-carbonyl-alpha-D-mannopyranosyl bromide with benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranoside (2) gave an alpha-D-linked disaccharide, further transformed by removal of the carbonyl and benzylidene groups and acetylation into the previously reported benzyl 2-acetamido-4,6-O-benzylidene groups and acetylation into the previously reported benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D-glucopyranoside. Condensation of 3,4,6-tri-O-benzyl-1,2,-O-(l-ethoxyethylidene)-alpha-D-glucopyranose or 2-O-acetyl-3,4,6-tri-O-benzyl-alpha-D-glucopyranosyl bromide with 2 gave benzyl 2-acetamido-3-O-(2 O-acetyl-3,4,6-tri-O-benzyl-beta-D-glucopyranosyl)-4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranoside. Removal of the acetyl group at O-2, followed by oxidation with acetic anhydride-dimethyl sulfoxide, gave the beta-D-arabino-hexosid-2-ulose 14. Reduction with sodium borohydride, and removal of the protective groups, gave 2-acetamido-2-deoxy-3-O-beta-D-mannopyranosyl-D-glucose, which was characterized as the heptaacetate. The anomeric configuration of the glycosidic linkage was ascertained by comparison with the alpha-D-linked analog.
4,6-二-O-乙酰基-2,3-O-羰基-α-D-甘露吡喃糖基溴与苄基 2-乙酰氨基-4,6-O-亚苄基-2-脱氧-α-D-吡喃葡萄糖苷（2）缩合得到一个α-D-连接的二糖，通过去除羰基和亚苄基并乙酰化进一步转化为先前报道的苄基 2-乙酰氨基-4,6-O-亚苄基-2-脱氧-3-O-(2,3,4,6-四-O-乙酰基-α-D-甘露吡喃糖基)-α-D-吡喃葡萄糖苷。3,4,6-三-O-苄基-1,2-O-(1-乙氧基亚乙基)-α-D-吡喃葡萄糖或 2-O-乙酰基-3,4,6-三-O-苄基-α-D-吡喃葡萄糖基溴与 2 缩合得到苄基 2-乙酰氨基-3-O-(2-O-乙酰基-3,4,6-三-O-苄基-β-D-吡喃葡萄糖基)-4,6-O-亚苄基-2-脱氧-α-D-吡喃葡萄糖苷。去除 O-2 位的乙酰基，然后用乙酸酐-二甲基亚砜氧化，得到β-D-阿拉伯己糖-2-酮糖 14。用硼氢化钠还原并去除保护基，得到 2-乙酰氨基-2-脱氧-3-O-β-D-甘露吡喃糖基-D-葡萄糖，其被表征为七乙酸酯。通过与α-D-连接的类似物比较确定糖苷键的异头构型。
