4-hydroxybutyl β-D-glucopyranoside | 59080-43-2

• 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: 4-hydroxybutyl β-D-glucopyranoside
• 英文别名: (4-Hydroxy-butyl)-β-D-glucopyranosid；(2R,3R,4S,5S,6R)-2-(4-hydroxybutoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 59080-43-2
• 化学式: C₁₀H₂₀O₇
• 分子量: 252.265
• InChiKey: HLEYNJGFQFYNQQ-HOTMZDKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-penten-1-yl-β-D-glucopyranoside 在 臭氧 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以91%的产率得到4-hydroxybutyl β-D-glucopyranoside
  参考文献：
  名称：

  Use of n-Pentenyl Glycosides as Precursors to Various Spacer Functionalities

  摘要：

  Pent-4-enyl beta-D-glucopyranoside and its peracetylated and perbenzylated derivatives are shown to be excellent substrates for preparation of a wide variety of spacer functionalities. The spacer derivatives so obtained are promising substrates for preparing agents such as neo-glycoconjugates, micelles, and liquid crystalline phases, which are of interest for studying various biological and physiological phenomena of carbohydrates.

  DOI：

  10.1021/jo9909554

文献信息

• Helferich; Hiltmann, Justus Liebigs Annalen der Chemie, 1937, vol. 531, p. 160,171, 175
  作者：Helferich、Hiltmann

  DOI：——

  日期：——
• Enzymatic glycosidations in dry media on mineral supports
  作者：Mirjana Gelo-Pujic、Eryka Guibé-Jampel、André Loupy

  DOI：10.1016/s0040-4020(97)10177-6

  日期：1997.12

  Preparation of 4-hydroxybutyl-beta-D-glucoside was achieved by reversed hydrolysis from glucose using almond-beta-glucosidase impregnated on mineral supports, while 4-hydroxybutyl-alpha-D-glucoside was obtained from glucose or by one-pot starch hydrolysis followed by glucosidation catalysed by gamma-amylase (amyloglucosidase) from Rhizopus mold on celites. The influence of the support nature and of water activity were investigated in order to shift the equilibrium towards glycosidation. (C) 1997 Elsevier Science Ltd.
• Use of <i>n</i>-Pentenyl Glycosides as Precursors to Various Spacer Functionalities
  作者：Therese Buskas、Eva Söderberg、Peter Konradsson、Bert Fraser-Reid

  DOI：10.1021/jo9909554

  日期：2000.2.1

  Pent-4-enyl beta-D-glucopyranoside and its peracetylated and perbenzylated derivatives are shown to be excellent substrates for preparation of a wide variety of spacer functionalities. The spacer derivatives so obtained are promising substrates for preparing agents such as neo-glycoconjugates, micelles, and liquid crystalline phases, which are of interest for studying various biological and physiological phenomena of carbohydrates.