allyl 2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranoside | 685136-13-4

• 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: allyl 2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranoside
• 英文别名: [(2S,3S,4R,5R,6R)-5-acetyloxy-4-benzoyloxy-2-methyl-6-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 685136-13-4
• 化学式: C₂₅H₂₆O₈
• 分子量: 454.477
• InChiKey: DJVZKZWYBAFKMN-IMXRWDCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  allyl 2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranoside 在 palladium dichloride 三氟甲磺酸三甲基硅酯 、 sodium acetate 、 溶剂黄146 、 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 7.0h， 生成 phenyl 2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Trisaccharide of Incanoside from Caryopteris incana

  摘要：

  Trisaccharide phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl-(1 --> 2)-3,4-di-O-benzoyl-alpha-L-rhamnopyranosyl-(1 --> 3 --> 3)-2-O-acetyl-4,6-O-benzylidene-1-thio-beta-D-glucopyranoside, the sugar core of incanosides from Caryopteris incana (T-HUNB.), was synthesized via a concise route. The key step of this route involved the preparation of decisive disaccharide acceptor from the phenyl 2-acetyl-3,4-di-O-benzoyl-alpha-L-rhamnopyranosyl-(1 --> 3)-2-O-acetyl-4,6-O-benzylidene-1-thio-beta-D-glucopyranoside by regioselective and chemoselective deacetylation method.

  DOI：

  10.1081/scc-120027292
• 作为产物：
  描述：

  原乙酸三甲酯 、 L-rhamnopyranose 、 苯甲酰氯 、 烯丙醇 以66%的产率得到allyl 2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of Trisaccharide of Incanoside from Caryopteris incana

  摘要：

  Trisaccharide phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl-(1 --> 2)-3,4-di-O-benzoyl-alpha-L-rhamnopyranosyl-(1 --> 3 --> 3)-2-O-acetyl-4,6-O-benzylidene-1-thio-beta-D-glucopyranoside, the sugar core of incanosides from Caryopteris incana (T-HUNB.), was synthesized via a concise route. The key step of this route involved the preparation of decisive disaccharide acceptor from the phenyl 2-acetyl-3,4-di-O-benzoyl-alpha-L-rhamnopyranosyl-(1 --> 3)-2-O-acetyl-4,6-O-benzylidene-1-thio-beta-D-glucopyranoside by regioselective and chemoselective deacetylation method.

  DOI：

  10.1081/scc-120027292