Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-tetrahydro-pyran-4-yl ester | 870192-82-8

• 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: Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-tetrahydro-pyran-4-yl ester
• CAS: 870192-82-8
• 化学式: C₂₄H₃₉NO₁₀SSi
• 分子量: 561.726
• InChiKey: MCQNUKRUOBSJKO-SJCYFTRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  147.45
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-tetrahydro-pyran-4-yl ester 在 吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 三乙基硅基三氟甲磺酸酯 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成
  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：

  2,3,4,6-四-O-乙酰基-1-S-乙酰基-1-硫代吡喃己糖 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-tetrahydro-pyran-4-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