heptyl 1-thio-α-D-mannopyranoside | 67283-42-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: heptyl 1-thio-α-D-mannopyranoside
• 英文别名: (2R,3S,4S,5S,6R)-2-heptylsulfanyl-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 67283-42-5
• 化学式: C₁₃H₂₆O₅S
• 分子量: 294.412
• InChiKey: HPEGNLMTTNTJSP-NAWOPXAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  8
• 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-庚硫醇 在 三氯化铁 、 三甲胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 heptyl 1-thio-α-D-mannopyranoside
  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

文献信息

• The Antiadhesive Strategy in Crohn′s Disease: Orally Active Mannosides to Decolonize Pathogenic<i>Escherichia coli</i>from the Gut
  作者：Dimitri Alvarez Dorta、Adeline Sivignon、Thibaut Chalopin、Tetiana I. Dumych、Goedele Roos、Rostyslav O. Bilyy、David Deniaud、Eva-Maria Krammer、Jérome de Ruyck、Marc F. Lensink、Julie Bouckaert、Nicolas Barnich、Sébastien G. Gouin

  DOI：10.1002/cbic.201600018

  日期：2016.5.17

  Ready for take off? Adherent‐invasive E. coli (AIEC) were shown to promote the inflammation of the intestinal mucosa of patients with Crohn′s disease (CD). We have designed a small library of AIEC antiadhesives, one of which could decolonize AIEC from the gut of a transgenic CD mouse model. These might open new perspectives in the treatment of CD.

  准备起飞？粘附侵袭性大肠杆菌（AIEC）被证明可促进克罗恩病（CD）患者肠道粘膜的炎症。我们设计了一个小的AIEC抗粘剂库，其中一个库可以使AIEC从转基因CD小鼠模型的肠道中非克隆化。这些可能会为CD的治疗开辟新的视野。
• Insulin-like and insulin-antagonistic carbohydrate derivatives. Synthesis of ω-substituted-alkyl 1-thio-α-D-mannopyranosides
  作者：Philippe L. Durette、T.Y. Shen

  DOI：10.1016/s0008-6215(00)85382-3

  日期：1980.8
• 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.