通过恶唑啉法合成烯丙基 2-乙酰氨基-3,6-二-O-苄基-2-脱氧-α-D-吡喃葡萄糖苷和壳二糖衍生物。
The synthesis of allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside and of chitobiose derivatives by the oxazoline procedure.
作者信息
Warren C D, Jeanloz R W
出版信息
Carbohydr Res. 1977 Jan;53(1):67-84. doi: 10.1016/s0008-6215(00)85455-5.
Controlled, partial benzylation of allyl 2-acetamido-3-O-benzyl-2-deoxy-alpha-D-glucopyranoside gave a mixture of the 3,4-di-, 3,6-di- (15), and 3,4,6-tri-O-benzyl derivatives, the major product being 15. Condensation of 15 with 2-methyl-(3,4,6-tri-O-acetul-1,2-dideoxy-alpha-D-glucopyrano)-[2,1-d]-2-oxazoline gave a disaccharide which, after purification, removal of the allyl group, and hydrogenolysis of the benzyl substituents, gave 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-i-deoxy-beta-D-glucopyranosyl)-2-deoxy-alpha-D-glucopyranose. This compound was further converted into di-N-acetyl-hexa-O-acetylchitobiose by acetylation, or into 2-methyl-[4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-3,6-di-O-acetyl-1,2-di-deoxy-alpha-D-glucopyrano]-[2,1-d]-2-oxazoline, a starting material for the preparation of di-N-acetyl-alpha-chitobiosyl phsophate.
烯丙基 2-乙酰氨基-3-O-苄基-2-脱氧-α-D-吡喃葡萄糖苷的可控部分苄基化反应得到了 3,4-二-O-苄基、3,6-二-O-苄基（15）和 3,4,6-三-O-苄基衍生物的混合物，主要产物为 15。15 与 2-甲基-(3,4,6-三-O-乙酰基-1,2-二脱氧-α-D-吡喃葡萄糖基)-[2,1-d]-2-恶唑啉缩合得到一种二糖，经过纯化、烯丙基的去除以及苄基取代基的氢解后，得到 2-乙酰氨基-4-O-(2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖基)-2-脱氧-α-D-吡喃葡萄糖。该化合物通过乙酰化进一步转化为二-N-乙酰基-六-O-乙酰基壳二糖，或转化为 2-甲基-[4-O-(2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖基)-3,6-二-O-乙酰基-1,2-二脱氧-α-D-吡喃葡萄糖基]-[2,1-d]-2-恶唑啉，一种用于制备二-N-乙酰基-α-壳二糖基磷酸酯的起始原料。
Zotero 插件