2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl trichloroacetimidate | 648885-50-1

• 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: 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: [(2R,3R,4S,5R,6S)-6-[[(2R,4aR,6R,7R,8S,8aR)-7-benzoyloxy-2-phenyl-6-(2,2,2-trichloroethanimidoyl)oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 648885-50-1
• 化学式: C₅₆H₄₆Cl₃NO₁₆
• 分子量: 1095.34
• InChiKey: VPCBBPHJAGKUIP-KQHFSGPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  76
• 可旋转键数：
  21
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  211
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2,4,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-glucopyranoside 、 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl trichloroacetimidate 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51%的产率得到4-methoxyphenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 3,6‐Branched β‐d‐Glucose Oligosaccharides

  摘要：

  A glucohexasaccharide, beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->6)]-beta(..)D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp was synthesized as its 4-methoxyphenyl glycosidevia 2 + 2 + 2 strategy with benzylidenated glucose mono- and disaccharides as the key intermediates.

  DOI：

  10.1081/car-120026599
• 作为产物：
  描述：

  在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of 3,6‐Branched β‐d‐Glucose Oligosaccharides

  摘要：

  A glucohexasaccharide, beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->6)]-beta(..)D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp was synthesized as its 4-methoxyphenyl glycosidevia 2 + 2 + 2 strategy with benzylidenated glucose mono- and disaccharides as the key intermediates.

  DOI：

  10.1081/car-120026599

文献信息

• Synthesis of heptasaccharide and nonasaccharide analogues of the lentinan repeating unit
  作者：Guangbin Yang、Fanzuo Kong

  DOI：10.1016/j.carres.2004.11.005

  日期：2005.1

  The allyl glycoside beta-D-Glcp-(1 --> 3)-beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 6)]-beta-D-Glcp-(1 --> 3)-beta-D-Glcp-(1 --> 3)-[beta-D-Glcp(1 --> 6)]-alpha-D-Glcp (18) and the acetonyl glycoside of beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 6)]-beta-D-Glcp-(1 --> 3)-beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 6)]-beta-D-Glcp-(1 --> 3)-beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 6)]-alpha-D-Glcp (28) were synthesized as analogues of the lentinan heptaose repeating unit. 4,6-O-Benzylidenated monosaccharide donor 3 and 4,6-0-benzylidenated tetrasaccharide acceptor 14 were used to ensure the P-linkage in the synthesis of 18, while 4,6-0-benzylidenated disaccharide acceptor 20, and 4,6-0-benzylidenated disaccharide donors 21 and 24 were used to ensure the beta-linkage in the synthesis of 28. (C) 2004 Elsevier Ltd. All rights reserved.