cyclohexyl-β-D-galactopyranoside | 39824-24-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexyl-β-D-galactopyranoside
• 英文别名: cyclohexyl β-D-galactoside；(2R,3R,4S,5R,6R)-2-cyclohexyloxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 39824-24-3
• 化学式: C₁₂H₂₂O₆
• 分子量: 262.303
• InChiKey: PUEQSGBQJWWOQJ-YBXAARCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 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 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 cyclohexyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Deoxy Derivatives of Lactose and their Hydrolysis by beta-Galactosidase from E. Coli.

  摘要：

  Methyl 2-deoxy-alpha-lactoside, methyl 3-deoxy-beta-lactoside, 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-glucitol and the 2-deoxy and 2,3-dideoxy derivatives of 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-glucitol have been synthesized by deoxygenation of lactose derivatives at appropriate positions. Cyclohexyl beta-D-galactopyranoside has also been synthesized. All derivatives proved to be substrates for the enzyme beta-galactosidase from E. coli, but the rate of hydrolysis of the substrate analogues was strongly dependent on the nature of the aglycone.

  DOI：

  10.3891/acta.chem.scand.46-0186

文献信息

• Ooi, Yasuhiro; Hashimoto, Toshihiro; Mitsuo, Naoki, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 4, p. 1808 - 1814
  作者：Ooi, Yasuhiro、Hashimoto, Toshihiro、Mitsuo, Naoki、Satoh, Toshio

  DOI：——

  日期：——
• Glycosylation Using Unprotected Alkynyl Donors
  作者：Sreeman K. Mamidyala、M.G. Finn

  DOI：10.1021/jo901857x

  日期：2009.11.6

  Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in acetonitrile with 5% AuCl(3) for reaction with various primary alcohol acceptors, the latter used in 10-fold molar excess relative to donor. Donors containing the 2-butynyl group were more reactive, giving good yields of glycoside products at lower temperatures Secondary alcohols could also be used but with diminished efficiency. The propargylic family of donors is especially convenient because they can be easily prepared on large scale by Fischer glycosylation and stored indefinitely before chemoselective activation by the catalyst.