6-benzyloxycarbonylaminohexyl β-D-galactopyranoside | 201737-04-4

• 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 β-D-galactopyranoside
• CAS: 201737-04-4
• 化学式: C₂₀H₃₁NO₈
• 分子量: 413.468
• InChiKey: XNJPRGYOVBDSRW-ICBNADEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.29
• 重原子数：
  29.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  137.71
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6-benzyloxycarbonylaminohexyl β-D-galactopyranoside 在 palladium on activated charcoal 氢气 、 三氧化硫吡啶 作用下， 以 吡啶 、 甲酸 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.5h， 生成 sodium 6-aminohexyl β-D-galactopyranoside 3-sulfate
  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：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 sodium methylate 、 氰化汞 、 mercury dibromide 作用下， 以 甲醇 、 硝基甲烷 、 甲苯 为溶剂， 反应 18.0h， 生成 6-benzyloxycarbonylaminohexyl 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

文献信息

• First Intramolecular Aglycon Delivery onto a D-Fucofuranosyl Entity for the Synthesis of α-D-Fucofuranose-Containing Disaccharides
  作者：Muriel Gelin、Vincent Ferrières、Martine Lefeuvre、Daniel Plusquellec

  DOI：10.1002/ejoc.200390184

  日期：2003.3

  Intramolecular aglycon delivery was performed for the first time starting from n-pentenyl glycofuranoside as a donor. p-Methoxybenzyl-assisted aglycon transfer required very mild reaction conditions and was promoted by N-iodosuccinimide without assistance of any Lewis acid catalyst. As a result, rare α-D-fucofuranose-containing disaccharides were obtained. Moreover, structure elucidation led to the

  首次以正戊烯基呋喃糖苷为供体进行分子内苷元递送。对甲氧基苄基辅助苷元转移需要非常温和的反应条件，并由 N-碘代琥珀酰亚胺促进，无需任何路易斯酸催化剂的帮助。结果，获得了罕见的含α-D-岩藻糖呋喃糖的二糖。此外，结构解析得出的结论是 N-琥珀酰亚胺残基仍然存在于所得产物中。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)