(2S,3S,4aS,7S,8R,8aR)-7-hydroxy-2,3-dimethoxy-8-((pmethoxybenzyl)oxy)-2,3-dimethylhexahydrobenzo[b][1,4]dioxin-5-(4aH)-one | 1392067-14-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,4aS,7S,8R,8aR)-7-hydroxy-2,3-dimethoxy-8-((pmethoxybenzyl)oxy)-2,3-dimethylhexahydrobenzo[b][1,4]dioxin-5-(4aH)-one
• 英文别名: (2S,3S,4aR,5R,6S,8aS)-6-hydroxy-2,3-dimethoxy-5-[(4-methoxyphenyl)methoxy]-2,3-dimethyl-5,6,7,8a-tetrahydro-4aH-benzo[b][1,4]dioxin-8-one
• CAS: 1392067-14-9
• 化学式: C₂₀H₂₈O₈
• 分子量: 396.438
• InChiKey: AIUMIOBPKIDWCK-IYHZHHKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3S,4aS,7S,8R,8aR)-7-hydroxy-2,3-dimethoxy-8-((pmethoxybenzyl)oxy)-2,3-dimethylhexahydrobenzo[b][1,4]dioxin-5-(4aH)-one 在 吡啶 、 正丁基锂 、 双氧水 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.34h， 生成 6-O-acetyl-2-azido-1-O-Benzyl-2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-β-L-gulopyranoside
  参考文献：
  名称：

  Syntheses of Carbocyclic Analogues of α-d-Glucosamine, α-d-Mannose, α-d-Mannuronic Acid, β-l-Idosamine, and β-l-Gulose

  摘要：

  A versatile synthesis of orthogonally protected derivatives of carba-alpha-D-glucosamine, carba-alpha-D-mannose, carba-alpha-D-mannuronic acid, carba-beta-L-idosamine, and carba-beta-L-gulose from methyl alpha-D-mannoside is described. Our synthetic strategy utilizes the palladium-promoted Ferrier carbocyclization and persistent butane-2,3-diacetal protection to produce a key chiral cyclohexanone intermediate, from which all five carbasugar derivatives can readily be obtained.

  DOI：

  10.1021/jo301240j
• 作为产物：
  描述：

  methyl 6-deoxy-2-O-(p-methoxy)benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-D-lyxo-hex-5-enopyranoside 在 palladium dichloride 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 以89%的产率得到(2S,3S,4aS,7S,8R,8aR)-7-hydroxy-2,3-dimethoxy-8-((pmethoxybenzyl)oxy)-2,3-dimethylhexahydrobenzo[b][1,4]dioxin-5-(4aH)-one
  参考文献：
  名称：

  Syntheses of Carbocyclic Analogues of α-d-Glucosamine, α-d-Mannose, α-d-Mannuronic Acid, β-l-Idosamine, and β-l-Gulose

  摘要：

  A versatile synthesis of orthogonally protected derivatives of carba-alpha-D-glucosamine, carba-alpha-D-mannose, carba-alpha-D-mannuronic acid, carba-beta-L-idosamine, and carba-beta-L-gulose from methyl alpha-D-mannoside is described. Our synthetic strategy utilizes the palladium-promoted Ferrier carbocyclization and persistent butane-2,3-diacetal protection to produce a key chiral cyclohexanone intermediate, from which all five carbasugar derivatives can readily be obtained.

  DOI：

  10.1021/jo301240j