methylthiomethyl 1-thio-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methylthiomethyl 1-thio-β-D-glucopyranoside
• 英文别名: afrostyraxthioside A；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(methylsulfanylmethylsulfanyl)oxane-3,4,5-triol
• 化学式: C₈H₁₆O₅S₂
• 分子量: 256.344
• InChiKey: PAIFKDJENKMXFI-CBQIKETKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methylthiomethyl 1-thio-β-D-glucopyranoside 、 乙酸酐 在 吡啶 作用下， 反应 20.0h， 以84%的产率得到methylthiomethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Three 1-thio-β-d-glucopyranosides from the seeds of Afrostyrax lepidophyllus Mildbr.

  摘要：

  Three new 1-thioglycosides namely methylthiomethyl 1-thio-beta-D-glucopyranoside (Afrostyraxthioside A), methylsulfonylmethyl 1-thio-beta-D-glucopyranoside (Afrostyraxthioside B) and methylsulfonylmethylthiomethyl 1-thio-beta-D-glucopyranoside (Afrostyraxthioside C) were isolated from the seeds of Afrostyrax lepidophyllus Mildbr. Their structures were mainly elucidated by using one- and two-dimensional NMR and mass spectroscopies and also by an efficient one-step synthesis. Moreover, Afrostyraxthiosides A, B and C constitute a new subclass of 1-thioglycosides isolated from natural sources. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.09.021
• 作为产物：
  描述：

  氯甲基甲硫醚 、 sodium 1-thio-β-D-glucopyranoside 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以73%的产率得到methylthiomethyl 1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Three 1-thio-β-d-glucopyranosides from the seeds of Afrostyrax lepidophyllus Mildbr.

  摘要：

  Three new 1-thioglycosides namely methylthiomethyl 1-thio-beta-D-glucopyranoside (Afrostyraxthioside A), methylsulfonylmethyl 1-thio-beta-D-glucopyranoside (Afrostyraxthioside B) and methylsulfonylmethylthiomethyl 1-thio-beta-D-glucopyranoside (Afrostyraxthioside C) were isolated from the seeds of Afrostyrax lepidophyllus Mildbr. Their structures were mainly elucidated by using one- and two-dimensional NMR and mass spectroscopies and also by an efficient one-step synthesis. Moreover, Afrostyraxthiosides A, B and C constitute a new subclass of 1-thioglycosides isolated from natural sources. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.09.021

文献信息

• Three 1-thio-β-d-glucopyranosides from the seeds of Afrostyrax lepidophyllus Mildbr.
  作者：Annie Ngono Ngane、Marie Lavault、Denis Séraphin、Anne Landreau、Pascal Richomme

  DOI：10.1016/j.carres.2006.09.021

  日期：2006.12

  Three new 1-thioglycosides namely methylthiomethyl 1-thio-beta-D-glucopyranoside (Afrostyraxthioside A), methylsulfonylmethyl 1-thio-beta-D-glucopyranoside (Afrostyraxthioside B) and methylsulfonylmethylthiomethyl 1-thio-beta-D-glucopyranoside (Afrostyraxthioside C) were isolated from the seeds of Afrostyrax lepidophyllus Mildbr. Their structures were mainly elucidated by using one- and two-dimensional NMR and mass spectroscopies and also by an efficient one-step synthesis. Moreover, Afrostyraxthiosides A, B and C constitute a new subclass of 1-thioglycosides isolated from natural sources. (c) 2006 Elsevier Ltd. All rights reserved.