2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-1,2-O-(R,S)-ethylidene-α-D-glucopyranose | 313220-19-8

• 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: 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-1,2-O-(R,S)-ethylidene-α-D-glucopyranose
• 英文别名: [(2R,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-[[(1R,3R,7R,8S,9R,11R)-5-methyl-11-phenyl-2,4,6,10,12-pentaoxatricyclo[7.4.0.03,7]tridecan-8-yl]oxy]oxan-2-yl]methyl benzoate
• CAS: 313220-19-8
• 化学式: C₄₉H₄₄O₁₅
• 分子量: 872.879
• InChiKey: FYYUAMBXFOABNT-BFWPQWJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  64
• 可旋转键数：
  16
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-1,2-O-(R,S)-ethylidene-α-D-glucopyranose 在 二氯乙酸 、 水 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以91%的产率得到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
• 作为产物：
  描述：

  苯甲醛二乙缩醛 在 三氟甲磺酸三甲基硅酯 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-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