6-hexylthio-6-deoxy-α-D-glucoside de methyle | 136317-26-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-hexylthio-6-deoxy-α-D-glucoside de methyle
• 英文别名: (2S,3S,4S,5R,6S)-2-(hexylsulfanylmethyl)-6-methoxyoxane-3,4,5-triol
• CAS: 136317-26-5
• 化学式: C₁₃H₂₆O₅S
• 分子量: 294.412
• InChiKey: AYRFYTSEUVDOED-LBELIVKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-hexylthio-6-deoxy-α-D-glucoside de methyle 在 间氯过氧苯甲酸 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以45%的产率得到6-hexylsulfonyl-6-deoxy-α-D-glucoside de methyle
  参考文献：
  名称：

  Synthese de nouveaux tensioactifs glycosidiques par l'intermediaire de sucres halogenes. Thioethers et sulfones derives de l'α-d-glucoside et l'α-d-mannoside de methyle.

  摘要：

  We describe an efficient synthesis of methyl 6-halogeno-6-deoxyglycosides which was performed using Ph3P-X2 in DMF solution. Carbohydrate halides could thus be isolated in high yields without preliminary protection of the secondary hydroxyl groups, and were used as intermediates for the preparation of 6-alkylthio- and 6-alkylsulfonyl-6-deoxy glycosides. These derivatives are new non-ionic chiral surfactants.

  DOI：

  10.1016/s0040-4020(01)87130-1
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 溴 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 6-hexylthio-6-deoxy-α-D-glucoside de methyle
  参考文献：
  名称：

  Synthese de nouveaux tensioactifs glycosidiques par l'intermediaire de sucres halogenes. Thioethers et sulfones derives de l'α-d-glucoside et l'α-d-mannoside de methyle.

  摘要：

  We describe an efficient synthesis of methyl 6-halogeno-6-deoxyglycosides which was performed using Ph3P-X2 in DMF solution. Carbohydrate halides could thus be isolated in high yields without preliminary protection of the secondary hydroxyl groups, and were used as intermediates for the preparation of 6-alkylthio- and 6-alkylsulfonyl-6-deoxy glycosides. These derivatives are new non-ionic chiral surfactants.

  DOI：

  10.1016/s0040-4020(01)87130-1

文献信息

• Synthese de nouveaux tensioactifs glycosidiques par l'intermediaire de sucres halogenes. Thioethers et sulfones derives de l'α-d-glucoside et l'α-d-mannoside de methyle.
  作者：Pascale Leon-Ruaud、Daniel Plusquellec

  DOI：10.1016/s0040-4020(01)87130-1

  日期：1991.1

  We describe an efficient synthesis of methyl 6-halogeno-6-deoxyglycosides which was performed using Ph3P-X2 in DMF solution. Carbohydrate halides could thus be isolated in high yields without preliminary protection of the secondary hydroxyl groups, and were used as intermediates for the preparation of 6-alkylthio- and 6-alkylsulfonyl-6-deoxy glycosides. These derivatives are new non-ionic chiral surfactants.