Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(2-methoxy-phenylsulfanyl)-tetrahydro-pyran-3-yl ester | 220691-84-9

• 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)-4,5-diacetoxy-6-acetoxymethyl-2-(2-methoxy-phenylsulfanyl)-tetrahydro-pyran-3-yl ester
• CAS: 220691-84-9
• 化学式: C₂₁H₂₆O₁₀S
• 分子量: 470.497
• InChiKey: CYDCBXINWAKGDO-BVJIBDCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  123.66
• 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 (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(2-methoxy-phenylsulfanyl)-tetrahydro-pyran-3-yl ester 在 甲醇 、 camphor-10-sulfonic acid 、 potassium tert-butylate 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Ley, Steven V.; Humphries, Alexander C.; Eick, Holger, Journal of the Chemical Society. Perkin transactions I, 1998, # 23, p. 3907 - 3911

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲氧基苯硫酚 、 1,2,3,4,6-O-五乙酰基-Alpha-甘露糖 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(2-methoxy-phenylsulfanyl)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Ley, Steven V.; Humphries, Alexander C.; Eick, Holger, Journal of the Chemical Society. Perkin transactions I, 1998, # 23, p. 3907 - 3911

  摘要：

  DOI：

文献信息

• Concise Synthesis of the C15–C38 Fragment of Okadaic Acid: Application of the Suzuki–Miyaura Reaction to Spiroacetal Synthesis
  作者：Haruhiko Fuwa、Keita Sakamoto、Takashi Muto、Makoto Sasaki

  DOI：10.1021/ol503491t

  日期：2015.1.16

  A concise synthetic entry to the C15-C38 fragment of okadaic acid by exploiting a Suzuki-Miyaura reaction for the rapid assembly of the spiroacetal substructures has been developed. The present synthesis was completed in 19 linear steps from a commercially available material, showcasing the efficiency of our synthetic strategy.
• Concise synthesis of the C15–C38 fragment of okadaic acid, a specific inhibitor of protein phosphatases 1 and 2A
  作者：Haruhiko Fuwa、Keita Sakamoto、Takashi Muto、Makoto Sasaki

  DOI：10.1016/j.tet.2015.04.001

  日期：2015.9

  A marine polyether natural product okadaic acid is known to be a potent and specific inhibitor of protein phosphatases 1 and 2A. Herein, concise synthesis of the C15-C38 fragment of okadaic acid is reported. We investigated two different strategies for the construction of two spiroacetal substructures found in the target compound. The first strategy involved Suzuki Miyaura coupling for the synthesis of endocyclic enol ethers and subsequent spiroacetalization. The second strategy exploited Suzuki-Miyaura coupling for the synthesis of exo-olefins as the precursor of spiroacetals. An alkynylaluminum-anomeric sulfone coupling effectively assembled the key spiroacetal substructures and completed the target compound. (C) 2015 Elsevier Ltd. All rights reserved.