allyl α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside | 242473-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside
• CAS: 242473-78-5
• 化学式: C₂₉H₃₄O₁₁
• 分子量: 558.582
• InChiKey: WWDROYHGYGMVKM-UENLNRIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  150.21
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  allyl α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 在 对甲苯磺酸 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 16.0h， 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
• 作为产物：
  描述：

  Allyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 在 甲醇 、 乙酰氯 作用下， 以90%的产率得到allyl α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  The Regio- and Stereoselective Synthesis of Rhamnose-Containing OligosaccharidesViaSugar-Sugar Orthoester Formation and Rearrangement

  摘要：

  Convenient regio- and stereoselective syntheses of rhamnose-containing oligosaccharides via sugar-sugar orthoester formation and rearrangement are described. 1-->3 Linked rhamno di- and trisaccharides were synthesized effectively using unprotected rhamnose residue as the glycosyl acceptor by this methodology.

  DOI：

  10.1080/07328309908544027