3-O-allyl-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl trichloroacetimidate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 3-O-allyl-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: [(4aR,6R,7R,8S,8aR)-2-phenyl-8-prop-2-enoxy-6-(2,2,2-trichloroethanimidoyl)oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] benzoate
• 化学式: C₂₅H₂₄Cl₃NO₇
• 分子量: 556.827
• InChiKey: NRKYTFABZGBWNW-WHTVCUERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-O-allyl-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis of two heptasaccharide analogues of the lentinan repeating unit

  摘要：

  beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->6)]-beta-D-Glcp (18) and the allyl 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-->3)[-beta-D-Glcp-(1-->6)]-alpha-D-Glcp (29) were synthesized as the analogues of the lentinan repeating heptaose by building the pentasaccharide backbones first, followed by attaching the side chains. 4,6-O-Benzylidenated mono-13 or disaccharide 8 were used as the acceptor to ensure the beta linkage in the synthesis of 18, while 4,6-O-benzylidenated disaccharides 21 and 23 were used as the donor and acceptor, respectively, to ensure the beta linkage in the synthesis of 29. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.08.003
• 作为产物：
  描述：

  (2S,3R,4S,5R,6R)-4-Allyloxy-6-hydroxymethyl-tetrahydro-pyran-2,3,5-triol 在 吡啶 、 氨 、 potassium carbonate 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 40.0h， 生成 3-O-allyl-2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of two heptasaccharide analogues of the lentinan repeating unit

  摘要：

  beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->6)]-beta-D-Glcp (18) and the allyl 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-->3)[-beta-D-Glcp-(1-->6)]-alpha-D-Glcp (29) were synthesized as the analogues of the lentinan repeating heptaose by building the pentasaccharide backbones first, followed by attaching the side chains. 4,6-O-Benzylidenated mono-13 or disaccharide 8 were used as the acceptor to ensure the beta linkage in the synthesis of 18, while 4,6-O-benzylidenated disaccharides 21 and 23 were used as the donor and acceptor, respectively, to ensure the beta linkage in the synthesis of 29. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.08.003

文献信息

• Synthesis of two heptasaccharide analogues of the lentinan repeating unit
  作者：Wei Zhao、Guangbin Yang、Fanzuo Kong

  DOI：10.1016/j.carres.2003.08.003

  日期：2003.11

  beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->6)]-beta-D-Glcp (18) and the allyl 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-->3)[-beta-D-Glcp-(1-->6)]-alpha-D-Glcp (29) were synthesized as the analogues of the lentinan repeating heptaose by building the pentasaccharide backbones first, followed by attaching the side chains. 4,6-O-Benzylidenated mono-13 or disaccharide 8 were used as the acceptor to ensure the beta linkage in the synthesis of 18, while 4,6-O-benzylidenated disaccharides 21 and 23 were used as the donor and acceptor, respectively, to ensure the beta linkage in the synthesis of 29. (C) 2003 Elsevier Ltd. All rights reserved.