Acetic acid (2S,4aR,6R,7R,8S,8aS)-7-acetoxy-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester | 870192-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: Acetic acid (2S,4aR,6R,7R,8S,8aS)-7-acetoxy-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
• CAS: 870192-83-9
• 化学式: C₂₈H₄₁NO₉SSi
• 分子量: 595.786
• InChiKey: VHBRAKWCDDWDQM-PXHMPXEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  122.54
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,4aR,6R,7R,8S,8aS)-7-acetoxy-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 在 4 A molecular sieve 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3R,4R,5R,6S)-4,5-Diacetoxy-3-((2R,3R,4S,5S,6R)-3,4-diacetoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Design, synthesis, and enzymatic property of a sulfur-substituted analogue of trigalacturonic acid

  摘要：

  A sulfur-substituted analogue of trigalacturonic acid (3) was synthesized. The synthesis features the application of 3-cyano-3-(tert-butyldimethylsilyl)oxypropylthioether (CSP) as a novel protective group for thiols. This analogue was designed with the expectation that it would be a stable analogous substrate for endo-polygalacturonase isolated from Stereum purpureum based on computer modeling experiments. Surface plasmon resonance experiments revealed that 3 forms a stable complex with the target enzyme. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.019
• 作为产物：
  描述：

  2-(tert-Butyl-dimethyl-silanyloxy)-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-butyronitrile 在 吡啶 、 camphor-10-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Acetic acid (2S,4aR,6R,7R,8S,8aS)-7-acetoxy-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
  参考文献：
  名称：

  Design, synthesis, and enzymatic property of a sulfur-substituted analogue of trigalacturonic acid

  摘要：

  A sulfur-substituted analogue of trigalacturonic acid (3) was synthesized. The synthesis features the application of 3-cyano-3-(tert-butyldimethylsilyl)oxypropylthioether (CSP) as a novel protective group for thiols. This analogue was designed with the expectation that it would be a stable analogous substrate for endo-polygalacturonase isolated from Stereum purpureum based on computer modeling experiments. Surface plasmon resonance experiments revealed that 3 forms a stable complex with the target enzyme. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.019