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 | 679812-45-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: [(2S,3S,4R,5R,6S)-6-[[(2R,4aR,6S,7R,8S,8aR)-7-acetyloxy-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-5-acetyloxy-4-benzoyloxy-2-methyloxan-3-yl] benzoate
• CAS: 679812-45-4
• 化学式: C₄₃H₄₂O₁₃S
• 分子量: 798.865
• InChiKey: KCLBBGCVNKEGLH-OYHGIGEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  57
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  177
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  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 在 三氟化硼乙醚 、 一水合肼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-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：

  allyl 2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate 在 吡啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 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

文献信息

• An Efficient and Regioselective Deprotection Method for Acetylated Glycosides
  作者：Jubiao Li、Yanguang Wang

  DOI：10.1081/scc-120027255

  日期：2004.1

  A new regioselective 2-O-deacetylation methodology of acetylated glycosides using 85% hydrazine hydrate in THF is described. Using this method, acetylated 1-thio-glycoside could also be selectively deprotected to give 3-O-deprotected compound.