Birch G G, Lee C K, Richardson A C, Ali Y
Carbohydr Res. 1976 Jul;49:153-61. doi: 10.1016/s0008-6215(00)83133-x.
Selective benzoylation of HO-2 and HO-2' of 4,6-O-benzylidene-alpha-D-glucopyranosyl 4,6-O-benzylidene-alpha-D-glucopyranoside with N-benzoylimidazole led to the exclusive formation of 2-O-benzoyl-4,6-O-benzylidene-alpha-D-glucopyranosyl 2-O-benzoyl-4,6-O-benzylidene-alpha-D-glucopyranoside. Oxidation of either the dibenzoate or the corresponding ditosylate with methyl sulphoxide--phosphorus pentaoxide gave the 3,3'-diulose, and subsequent reduction with borohydride gave the 3,3'diepimers having the allo-allo configuration. De-esterification and hydrolysis of the benzylidene substituents gave alpha-D-allopyranosyl alpha-D-allopyranoside.
用N-苯甲酰基咪唑对4,6-O-亚苄基-α-D-吡喃葡萄糖基4,6-O-亚苄基-α-D-吡喃葡萄糖苷的HO-2和HO-2'进行选择性苯甲酰化反应，专一性地生成了2-O-苯甲酰基-4,6-O-亚苄基-α-D-吡喃葡萄糖基2-O-苯甲酰基-4,6-O-亚苄基-α-D-吡喃葡萄糖苷。用二甲亚砜 - 五氧化二磷氧化二苯甲酸酯或相应的二对甲苯磺酸酯得到3,3'-二酮糖，随后用硼氢化物还原得到具有阿洛 - 阿洛构型的3,3'-差向异构体。亚苄基取代基的脱酯和水解反应得到α-D-阿洛吡喃糖基α-D-阿洛吡喃糖苷。
