6-benzyloxycarbonylaminohexyl 2-O-acetyl-3-O-benzoyl-6-O-benzyl-β-D-galactopyranoside | 201737-12-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-benzyloxycarbonylaminohexyl 2-O-acetyl-3-O-benzoyl-6-O-benzyl-β-D-galactopyranoside
• CAS: 201737-12-4
• 化学式: C₃₆H₄₃NO₁₀
• 分子量: 649.738
• InChiKey: YDCOAINHRIPBMX-ATFNGGABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  47.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  138.85
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  6-benzyloxycarbonylaminohexyl 2-O-acetyl-3-O-benzoyl-6-O-benzyl-β-D-galactopyranoside 在 sodium methylate 、 三氧化硫吡啶 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis of a set of highly clustered monosulfated galactopyranosides

  摘要：

  There are several biological events that are known to involve certain sulfated saccharides. In many such cases, however, clustered ligands have been shown to be more effective than monovalent saccharides. A set of 6-aminohexyl glycosides of 2,3,4 or 6-monosulfated galactose have been synthesized and linked to polyglutamic acid. Because of the bulky aglycon employed, the 2-OH group of the key compound, 6-benzyloxycarbonylaminohexyl 4,6-O-benzylidene-beta-D-galactopyranoside was markedly less reactive than 3-OH. Thus, site-specific acetylation of 3-OH was readily carried out to obtain 2-O-sulfated galactosides, and even the direct sulfation of 3-OH afforded the 3-sulfate in a reasonable yield. On the other hand, the key compound was unexpectedly resistant to 2,3-O-dibenzylation or 2,3-O-dibenzoylation, both of which were meant for regioselective cleavage of 4,6-benzylidene to obtain the 4-sulfate. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(97)00240-1
• 作为产物：
  描述：

  6-benzyloxycarbonylaminohexyl β-D-galactopyranoside 在 吡啶 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲酸 为溶剂， 反应 7.5h， 生成 6-benzyloxycarbonylaminohexyl 2-O-acetyl-3-O-benzoyl-6-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a set of highly clustered monosulfated galactopyranosides

  摘要：

  There are several biological events that are known to involve certain sulfated saccharides. In many such cases, however, clustered ligands have been shown to be more effective than monovalent saccharides. A set of 6-aminohexyl glycosides of 2,3,4 or 6-monosulfated galactose have been synthesized and linked to polyglutamic acid. Because of the bulky aglycon employed, the 2-OH group of the key compound, 6-benzyloxycarbonylaminohexyl 4,6-O-benzylidene-beta-D-galactopyranoside was markedly less reactive than 3-OH. Thus, site-specific acetylation of 3-OH was readily carried out to obtain 2-O-sulfated galactosides, and even the direct sulfation of 3-OH afforded the 3-sulfate in a reasonable yield. On the other hand, the key compound was unexpectedly resistant to 2,3-O-dibenzylation or 2,3-O-dibenzoylation, both of which were meant for regioselective cleavage of 4,6-benzylidene to obtain the 4-sulfate. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(97)00240-1