(R)-4-((2R,3R,4S)-3-Benzyloxy-4-hydroxy-tetrahydro-thiophen-2-yl)-4-methoxy-butyric acid methyl ester | 183001-90-3

• 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: (R)-4-((2R,3R,4S)-3-Benzyloxy-4-hydroxy-tetrahydro-thiophen-2-yl)-4-methoxy-butyric acid methyl ester
• CAS: 183001-90-3
• 化学式: C₁₇H₂₄O₅S
• 分子量: 340.441
• InChiKey: YBZPMNIZLPATJV-MUIFIZLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-4-((2R,3R,4S)-3-Benzyloxy-4-hydroxy-tetrahydro-thiophen-2-yl)-4-methoxy-butyric acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以50%的产率得到(3S,4R,5R)-4-Benzyloxy-5-((R)-4-hydroxy-1-methoxy-butyl)-tetrahydro-thiophen-3-ol
  参考文献：
  名称：

  Enantiospecific synthesis of 8-O-methylthioswainsonine from a derivative of D-glucose

  摘要：

  The thioanalogue 1, (1R,2S,4S,8R,8 alpha S)-1,2,8-trihydroxy-8-O-methylthioindolizidine of 8-O-methylswainsonine 2 has been enantiospecifically synthesized from the important key intermediate methyl 2-O-methyl-3,6-thioanhydro-alpha-D-mannopyranoside 7, in five steps. Formation of the bicyclic system in 1 took place with a high stereoselectivity. Compound 7 was obtained in eight steps from the readily available methyl alpha-D-glucopyranoside. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00330-8
• 作为产物：
  描述：

  (E)-(R)-4-((2R,3R,4S)-3-Benzyloxy-4-hydroxy-tetrahydro-thiophen-2-yl)-4-methoxy-but-2-enoic acid methyl ester 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以67%的产率得到(R)-4-((2R,3R,4S)-3-Benzyloxy-4-hydroxy-tetrahydro-thiophen-2-yl)-4-methoxy-butyric acid methyl ester
  参考文献：
  名称：

  Enantiospecific synthesis of 8-O-methylthioswainsonine from a derivative of D-glucose

  摘要：

  The thioanalogue 1, (1R,2S,4S,8R,8 alpha S)-1,2,8-trihydroxy-8-O-methylthioindolizidine of 8-O-methylswainsonine 2 has been enantiospecifically synthesized from the important key intermediate methyl 2-O-methyl-3,6-thioanhydro-alpha-D-mannopyranoside 7, in five steps. Formation of the bicyclic system in 1 took place with a high stereoselectivity. Compound 7 was obtained in eight steps from the readily available methyl alpha-D-glucopyranoside. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00330-8