pentyl 1-thio-β-D-galactopyranoside | 50615-67-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pentyl 1-thio-β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-pentylsulfanyloxane-3,4,5-triol
• CAS: 50615-67-3
• 化学式: C₁₁H₂₂O₅S
• 分子量: 266.359
• InChiKey: XXNMZLWFXMAKLU-KJPMQGKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 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：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-pentylsulfanyl-tetrahydro-pyran-4-yl ester 在 三甲胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 pentyl 1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis, purification and liquid-crystalline behaviour of several alkyl 1-thio-d-glycopyranosides

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(97)00185-7