Synthesis of a peripheral trisaccharide sequence of lutropin, a pituitary glycoprotein hormone; use of chitobiose as a key starting material
作者:Shin-Ichiro Nishimura、Hiroyoshi Kuzuhara
DOI:10.1016/0008-6215(90)80061-7
日期:1990.10
benzyl-alpha-D-mannopyranoside (11) by use of a few reaction steps. The 4(3)-hydroxyl group of 11 was methanesulfonylated, and the product subjected to SN2 replacement with acetate anion, to give the D-galactosamine-containing trisaccharide derivative (12). After basic hydrolysis of 12, the 4(3)-hydroxyl group was sulfated, and all benzyl groups were removed by hydrogenolysis, giving methyl O-(2-a
壳二糖衍生物,甲基O-(3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺-β-D-吡喃葡萄糖基)-(1 --- -4)-3,6-二- O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-β-D-吡喃葡萄糖苷衍生自相应的N-乙酰基衍生物,并将其转化为糖基溴化物(5)。在三氟甲烷磺酸银的存在下,5与3,4,6-三-O-苄基-α-D-甘露吡喃糖甲基之间的糖基化反应产生了β-D-连接的三糖衍生物。N,N-邻苯二甲酰基被乙酰基取代后,生成的产物转化为甲基O-(2-乙酰氨基-3,6-二-O-苄基-2-脱氧-β-D-吡喃葡萄糖基)-( 1 ---- 4)-O-(2-乙酰氨基-3,6-二-O-苄基-2-脱氧-β-D-吡喃葡萄糖基)-(1 ---- 2)-3,4,6 -通过使用一些反应步骤,三-O-苄基-α-D-甘露吡喃糖苷(11)。11的4(3)-羟基被甲磺酰化,用乙酸根阴离子对产物进行SN2置换,得到含