allyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside | 578731-68-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside
• CAS: 578731-68-7
• 化学式: C₅₅H₅₄O₁₈
• 分子量: 1003.02
• InChiKey: VTJRQVNVBUAPDW-SFZPMTHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  73.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  227.34
• 氢给体数：
  2.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-α,β-D-xylopyranosyl trichloroacetimidate 、 allyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以79.9%的产率得到allyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->2)-[2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->4)]-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：

  allyl 2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 水 、 三氟乙酸 为溶剂， 反应 4.0h， 生成 allyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->4)-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