Wessel H P, Trumtel M
F. Hoffmann-La Roche Ltd., Pharma Division, Basel, Switzerland.
Carbohydr Res. 1997 Jan 2;297(2):163-8. doi: 10.1016/s0008-6215(96)00262-5.
Pivaloylation of maltose gave, in satisfactory yield, 1,2,6,2',3',4',6'-hepta-O-pivaloyl-beta-maltose which was converted to the 3-deoxygenated analogue in a Barton-McCombie reaction. This compound was used directly in a trimethylsilyl triflate-mediated glycosylation reaction with 2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-D-glucopyranoside to give the corresponding maltosyl-(1-->4)-alpha, alpha-trehalose derivative. After deprotection, the monodeoxygenated tetrasaccharide was sulfated; in the reaction product, one compound fully sulfated at the outer pyranose rings predominated.
麦芽糖的新戊酰化反应以令人满意的产率得到了1,2,6,2',3',4',6'-七-O-新戊酰基-β-麦芽糖，该产物在巴顿-麦康比反应中转化为3-脱氧类似物。此化合物直接用于三氟甲磺酸三甲基硅酯介导的糖基化反应，与2,3,6-三-O-苄基-α-D-吡喃葡萄糖基2,3-二-O-苄基-4,6-O-亚苄基-α-D-吡喃葡萄糖苷反应，得到相应的麦芽基-(1→4)-α,α-海藻糖衍生物。脱保护后，对单脱氧四糖进行硫酸化；在反应产物中，一种在外层吡喃糖环上完全硫酸化的化合物占主导。
