(4S,5R,6S)-4,5-Diacetoxy-6-isopropylsulfanyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester | 314079-43-1

• 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: (4S,5R,6S)-4,5-Diacetoxy-6-isopropylsulfanyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,3R,4S)-3,4-diacetyloxy-2-propan-2-ylsulfanyl-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 314079-43-1
• 化学式: C₁₄H₂₀O₇S
• 分子量: 332.375
• InChiKey: ZDYIHMQCMZLIPB-SUHUHFCYSA-N

物化性质

• 沸点：
  409.9±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S)-4,5-Diacetoxy-6-isopropylsulfanyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (4S,5R,6S)-4,5-Dihydroxy-6-isopropylsulfanyl-5,6-dihydro-4H-pyran-2-carboxylic acid
  参考文献：
  名称：

  Rapid access to uronic acid-based mimetics of Kdn2en from d-glucurono-6,3-lactone

  摘要：

  A concise route to novel mimetics of Kdn2en, based on Delta(4)-uronic acids, from D-glucurono-6,3-lactone is presented. Uronic acid-based mimetics in which an aliphatic ether (O-glycoside), a thioether (S-glycoside), or acetamide takes the place of the natural C-6 glycerol sidechain of the sialic acid were synthesized from the key intermediate, methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate bromide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00228-7
• 作为产物：
  描述：

  D-GLUCURONIDEMETHYLESTERD-葡糖苷酸甲酯 在 高氯酸 、 氢溴酸 、 二乙胺 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.0h， 生成 (4S,5R,6S)-4,5-Diacetoxy-6-isopropylsulfanyl-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Rapid access to uronic acid-based mimetics of Kdn2en from d-glucurono-6,3-lactone

  摘要：

  A concise route to novel mimetics of Kdn2en, based on Delta(4)-uronic acids, from D-glucurono-6,3-lactone is presented. Uronic acid-based mimetics in which an aliphatic ether (O-glycoside), a thioether (S-glycoside), or acetamide takes the place of the natural C-6 glycerol sidechain of the sialic acid were synthesized from the key intermediate, methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate bromide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00228-7