2-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4aR,6R,7R,8R,8aR)-7,8-dihydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylsulfanyl]-butyronitrile | 874634-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4aR,6R,7R,8R,8aR)-7,8-dihydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylsulfanyl]-butyronitrile
• CAS: 874634-84-1
• 化学式: C₂₄H₃₇NO₇SSi
• 分子量: 511.712
• InChiKey: OSZNATRLCXXGNL-KFRXNAIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  110.4
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4aR,6R,7R,8R,8aR)-7,8-dihydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylsulfanyl]-butyronitrile 在 吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 、 4 A molecular sieve 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 生成 (2S,3R,4R,5R,6R)-5-(((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-hydroxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)thio)-2-methoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4-diyl diacetate
  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：

  Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(3-oxo-propylsulfanyl)-tetrahydro-pyran-4-yl ester 在 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 2-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4aR,6R,7R,8R,8aR)-7,8-dihydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylsulfanyl]-butyronitrile
  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