methyl 4-O-<3-O-allyl-2,4-di-O-benzoyl-6-O-(4-methoxybenzyl)-β-D-mannopyranosyl>-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 129090-94-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-<3-O-allyl-2,4-di-O-benzoyl-6-O-(4-methoxybenzyl)-β-D-mannopyranosyl>-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-5-benzoyloxy-6-[(2R,3S,4R,5R,6R)-5-(1,3-dioxoisoindol-2-yl)-6-methoxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-[(4-methoxyphenyl)methoxymethyl]-4-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 129090-94-4
• 化学式: C₆₀H₅₉NO₁₅
• 分子量: 1034.13
• InChiKey: UCXIUXMAWVCORB-ICUIIUQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.18
• 重原子数：
  76.0
• 可旋转键数：
  23.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  173.05
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  [(2R,3S,4S,5R,6S)-6-[(2R,3S,4R,5R,6R)-5-(1,3-dioxoisoindol-2-yl)-6-methoxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-[(4-methoxyphenyl)methoxymethyl]-4-prop-2-enoxy-5-(trifluoromethylsulfonyloxy)oxan-3-yl] trifluoromethanesulfonate 生成 methyl 4-O-<3-O-allyl-2,4-di-O-benzoyl-6-O-(4-methoxybenzyl)-β-D-mannopyranosyl>-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  ALAIS, JOCELYNE;DAVID, SERGE, CARBOHYDR. RES., 201,(1990) N, C. 69-77

  摘要：

  DOI：

文献信息

• Preparation of disaccharides having a β-d-mannopyranosyl group from N-phthaloyllactosamine derivatives by double or triple SN2 substitution
  作者：Jocelyne Alais、Serge David

  DOI：10.1016/0008-6215(90)84225-j

  日期：1990.6

  6'-O-anisylidene derivative, to give the 6'-O-(4-methoxybenzyl) ether 15. Conversion of 8 and 15 to their 2',4'-bis(trifluoromethanesulfonates), followed by SN2 reaction with benzoate, gave the corresponding beta-D-mannopyranosyl disaccharides. However, the model methyl 3-O-allyl-beta-D-galactopyranoside and 9 were converted into beta-D-mannopyranosyl derivatives in better yield (52-55%) by a one-pot, triple

  1,2,3,4,6-戊基-O-乙酰基-β-D-吡喃半乳糖与3,6-二-O-苄基-2-脱氧-2-邻苯二甲酰亚胺基-β-D-吡喃葡萄糖苷甲基缩合通过碱性甲醇分解，得到具有未取代的β-D-吡喃半乳糖基的乳糖胺衍生物。三丁基氧化锡介导的烯丙基化产生的3'-O-烯丙基（9）收率高，3'，6'-二-O-烯丙基醚（8）收率低。通过还原性地打开4'，6'-O-苯二亚甲基衍生物，得到6'-O-（4-甲氧基苄基）醚15，可以在O-6'处保护9。将8和15转化为其2 '，4'-双（三氟甲磺酸酯），然后与苯甲酸酯进行SN2反应，得到相应的β-D-甘露吡喃糖基二糖。然而，