hexyl-(1-thio-β-D-galactopyranoside) | 51575-56-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: hexyl-(1-thio-β-D-galactopyranoside)
• 英文别名: Hexyl-(1-thio-β-D-galactopyranosid)；(2S,3R,4S,5R,6R)-2-hexylsulfanyl-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 51575-56-5
• 化学式: C₁₂H₂₄O₅S
• 分子量: 280.386
• InChiKey: ATFNYTMEOCLMPS-IIRVCBMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-己硫醇 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.5h， 生成 hexyl-(1-thio-β-D-galactopyranoside)
  参考文献：
  名称：

  Dahlhoff, Wilhelm V.; Radkowski, Karin; Riehl, Klaus, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1995, vol. 50, # 7, p. 1079 - 1085

  摘要：

  DOI：

文献信息

• Synthesis, purification and liquid-crystalline behaviour of several alkyl 1-thio-d-glycopyranosides
  作者：Saskia A. Galema、Jan B.F.N. Engberts、Henk A. van Doren

  DOI：10.1016/s0008-6215(97)00185-7

  日期：1997.10

  This paper describes the synthesis, purification, and liquid-crystalline behaviour of a series of alkyl 1-thioglycopyranosides. The synthesis of these derivatives was carried out via a Lewis acid mediated coupling of the fully acetylated monosaccharide with an alkanethiol. The choice of the Lewis acid depends on the configuration of AcO-2, The carbohydrate-derived surfactants exhibit thermotropic liquid-crystalline behaviour. The alkyl 1-thioglycopyranosides form the expected smectic A phases upon heating. The clearing temperatures vary with alkyl chain length which is in accordance with the accepted model for the S-A phase of amphiphilic carbohydrate mesogens. For the alkyl 1-thiotalopyranosides, the clearing points are much lower than expected, presumably due to the formation of an intramolecular hydrogen bond in the talose moiety. (C) 1997 Elsevier Science Ltd.
• Helferich; Tuerk, Chemische Berichte, 1956, vol. 89, p. 2215,2218
  作者：Helferich、Tuerk

  DOI：——

  日期：——