4-[(2S,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-3,5-dimethoxybenzoic acid | 187405-74-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 4-[(2S,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-3,5-dimethoxybenzoic acid
• CAS: 187405-74-9
• 化学式: C₃₆H₃₈O₁₀
• 分子量: 630.692
• InChiKey: XXXCQUHGCSRUOY-BDOIURIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-[(2S,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-3,5-dimethoxybenzoic acid 在 4-二甲氨基吡啶 、 MS 4 Angstroems 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到(3S,4R,5S,6R,7R,16S,17R,18S,19R,20R)-13,26,27,30-tetramethoxy-4,5,6,17,18,19-hexakis(phenylmethoxy)-2,9,15,22,29,32-hexaoxapentacyclo[22.2.2.211,14.13,7.116,20]dotriaconta-1(27),11(31),12,14(30),24(28),25-hexaene-10,23-dione
  参考文献：
  名称：

  Stereoselective Synthesis of a New Kind of Natural Glyco-Cyclophane

  摘要：

  A new kind of natural glyco-cyclophane, clemochinenoside-A (1), has been stereoselectively synthesized from 1,6-di-0-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose. 4-Dimethylaminopyridine and dicyclohexylcarbodiimide were first used to catalyze the glyco-cycloesterification.

  DOI：

  10.1080/00397919908086202
• 作为产物：
  描述：

  6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 4-[(2S,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-3,5-dimethoxybenzoic acid
  参考文献：
  名称：

  Stereoselective Synthesis of a New Kind of Natural Glyco-Cyclophane

  摘要：

  A new kind of natural glyco-cyclophane, clemochinenoside-A (1), has been stereoselectively synthesized from 1,6-di-0-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose. 4-Dimethylaminopyridine and dicyclohexylcarbodiimide were first used to catalyze the glyco-cycloesterification.

  DOI：

  10.1080/00397919908086202

文献信息

• Stereoselective Synthesis of a New Kind of Natural Glyco-Cyclophane
  作者：Yulan Wang、Jianmin Mao、Mengshen Cai

  DOI：10.1080/00397919908086202

  日期：1999.6

  A new kind of natural glyco-cyclophane, clemochinenoside-A (1), has been stereoselectively synthesized from 1,6-di-0-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose. 4-Dimethylaminopyridine and dicyclohexylcarbodiimide were first used to catalyze the glyco-cycloesterification.