2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate | 578731-60-9

• 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-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate
• CAS: 578731-60-9
• 化学式: C₆₉H₆₀Cl₃NO₂₀
• 分子量: 1329.59
• InChiKey: WWQRUAJYEQZYQQ-PVZQENLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.93
• 重原子数：
  93.0
• 可旋转键数：
  19.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  263.33
• 氢给体数：
  1.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  methyl α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 、 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl 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57.3%的产率得到methyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Efficient synthesis of a heptasaccharide, the repeating unit of the O-chain lipopolysaccharide produced by Xanthomonas campestris strain 642

  摘要：

  alpha-L-Rhap-(1 --> 3)-alpha-L-Rhap-(1 --> 2)-alpha--L-Rhap-(1 --> 3)-[beta-D-Xylp-(1 --> 2)-][beta-D-Xylp-(1 --> 4)-]alpha-L-Rhap-(1 --> 3)-alpha-L-Rhap, the repeating unit of the O-chain lipopolysaccharide produced by Xanthomonas campestris strain 642 was synthesized as its methyl glycoside via 3-O-selective glycosylation of methyl alpha-L-rhamnopyranosyl-(1 --> 3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranoside (9) with 2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl-(1 --> 3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranosyl-(1 --> 2)-3,4-di-O-benzoyl-(alpha-L-rhamnopyranosyl trichloroacetimidate (8), followed by dixylosylation with 2,3,4-tri-O-benzoyl-alpha,beta-D-xylopyranosyl trichloroacetimidate (12) and subsequent deacylation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00080-6
• 作为产物：
  描述：

  2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 sodium acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 palladium dichloride 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 32.0h， 生成 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Efficient synthesis of a heptasaccharide, the repeating unit of the O-chain lipopolysaccharide produced by Xanthomonas campestris strain 642

  摘要：

  alpha-L-Rhap-(1 --> 3)-alpha-L-Rhap-(1 --> 2)-alpha--L-Rhap-(1 --> 3)-[beta-D-Xylp-(1 --> 2)-][beta-D-Xylp-(1 --> 4)-]alpha-L-Rhap-(1 --> 3)-alpha-L-Rhap, the repeating unit of the O-chain lipopolysaccharide produced by Xanthomonas campestris strain 642 was synthesized as its methyl glycoside via 3-O-selective glycosylation of methyl alpha-L-rhamnopyranosyl-(1 --> 3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranoside (9) with 2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl-(1 --> 3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranosyl-(1 --> 2)-3,4-di-O-benzoyl-(alpha-L-rhamnopyranosyl trichloroacetimidate (8), followed by dixylosylation with 2,3,4-tri-O-benzoyl-alpha,beta-D-xylopyranosyl trichloroacetimidate (12) and subsequent deacylation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00080-6