1,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-1,2-O-(R,S)-ethylidene-α-D-glucopyranose | 313220-20-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-1,2-O-(R,S)-ethylidene-α-D-glucopyranose
• 英文别名: [(2R,3R,4S,5S,6R)-6-[[(3aR,5R,6R,7S,7aR)-6-hydroxy-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-7-yl]oxy]-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 313220-20-1
• 化学式: C₄₂H₄₀O₁₅
• 分子量: 784.771
• InChiKey: RPAHFTZQAFMHQT-YNZPZXAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  192
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S,6S)-3,4,5-三苯甲酰氧基-6-(2,2,2-三氯亚氨代乙酰)氧基-四氢吡喃-2-基]甲基苯甲酸酯 、 1,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-1,2-O-(R,S)-ethylidene-α-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-1,2-O-(R,S)-ethylidene-α-D-glucopyranose
  参考文献：
  名称：

  A facile synthesis of the tetrasaccharide repeating unit of mannoglucan from Microellobosporia grisea

  摘要：

  A facile synthesis of the tetrasaccharide repeating unit of mannoglucan from Microellobosporia grisea was achieved through coupling of 4,6-O-benzylidene-1,2-O-ethylidene-alpha-D-glucopyranose with per-O-benzoylated mannopyranosyl trichloroacetimidate, followed by debenzylidenation, selective 6-O-mannopyranosylation, then hydrolysis of the 1,2-O-ethylidene group, 1,2-O-acetylation and conversion to the 1-trichloroacetimidate, and subsequent condensation of the activated trisaccharide with allyl 2,3,6-tri-0-benzoyl-alpha-D-glucopyranoside. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00160-9
• 作为产物：
  描述：

  4,6-O-benzylidene-1,2-O-(R,S)-ethylidene-α-D-glucopyranose 在 二氯乙酸 、 三氟甲磺酸三甲基硅酯 、 水 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 9.0h， 生成 1,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-1,2-O-(R,S)-ethylidene-α-D-glucopyranose
  参考文献：
  名称：

  A facile synthesis of the tetrasaccharide repeating unit of mannoglucan from Microellobosporia grisea

  摘要：

  A facile synthesis of the tetrasaccharide repeating unit of mannoglucan from Microellobosporia grisea was achieved through coupling of 4,6-O-benzylidene-1,2-O-ethylidene-alpha-D-glucopyranose with per-O-benzoylated mannopyranosyl trichloroacetimidate, followed by debenzylidenation, selective 6-O-mannopyranosylation, then hydrolysis of the 1,2-O-ethylidene group, 1,2-O-acetylation and conversion to the 1-trichloroacetimidate, and subsequent condensation of the activated trisaccharide with allyl 2,3,6-tri-0-benzoyl-alpha-D-glucopyranoside. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00160-9