{2-[(3aR,4S,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-thioacetylamino}-acetic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: {2-[(3aR,4S,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-thioacetylamino}-acetic acid
• 英文别名: 2-[[2-[(3aS,4R,6S,6aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]ethanethioyl]amino]acetic acid
• 化学式: C₁₆H₂₅NO₇S
• 分子量: 375.443
• InChiKey: OXGDHWUTAIUTRR-BYHUDHONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  96.8
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl)-N,N-(pentamethylene)ethanethioamide 在 吡啶 、 硫化氢 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 {2-[(3aR,4S,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-thioacetylamino}-acetic acid
  参考文献：
  名称：

  Synthesis of d -mannofuranosyl-ethanethioamides and the corresponding ethanedithioate, the first C -glycosyl derivative with thioacylating properties

  摘要：

  D-Mannofuranosyl-ethanethioamides were prepared in gold yields via a Homer-Wadsworth-Emmons reaction of thiocarbamoylmethylphosphonates with 2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranose. New glycosyl-ethanethioamides were obtained and one of them was converted into the corresponding dithioester which is a potential sugar substituted thioacylating agent for aminoacids. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00304-9

文献信息

• Synthesis of d -mannofuranosyl-ethanethioamides and the corresponding ethanedithioate, the first C -glycosyl derivative with thioacylating properties
  作者：Franck Sandrinelli、Sylvie Le Roy-Gourvennec、Serge Masson、Patrick Rollin

  DOI：10.1016/s0040-4039(98)00304-9

  日期：1998.4

  D-Mannofuranosyl-ethanethioamides were prepared in gold yields via a Homer-Wadsworth-Emmons reaction of thiocarbamoylmethylphosphonates with 2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranose. New glycosyl-ethanethioamides were obtained and one of them was converted into the corresponding dithioester which is a potential sugar substituted thioacylating agent for aminoacids. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.