(2S,3S)-3-((1R,2S,3R)-1,2,3-Tris-benzyloxy-4-hydroxy-butyl)-oxirane-2-carboxylic acid methyl ester | 215303-28-9

• 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)-3-((1R,2S,3R)-1,2,3-Tris-benzyloxy-4-hydroxy-butyl)-oxirane-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,3S)-3-[(1R,2S,3R)-4-hydroxy-1,2,3-tris(phenylmethoxy)butyl]oxirane-2-carboxylate
• CAS: 215303-28-9
• 化学式: C₂₉H₃₂O₇
• 分子量: 492.569
• InChiKey: CWPCMLDTWSAARU-VFHRMQJUSA-N

物化性质

• 沸点：
  633.373±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.233±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲氧羰基亚甲基三苯基正膦 、 (2S,3S)-3-((1R,2S,3R)-1,2,3-Tris-benzyloxy-4-hydroxy-butyl)-oxirane-2-carboxylic acid methyl ester 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (2S,3S)-3-((E)-(1R,2S,3R)-1,2,3-Tris-benzyloxy-5-methoxycarbonyl-pent-4-enyl)-oxirane-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Free Radical Studies and Solutions to the Synthesis of (+)-Cyclophellitol

  摘要：

  D-Xylose serves as a starting material for approaches to the synthesis of the glucosidase inhibitors, (+)-cyclophellitol (1) and (+)-epi-cyclophellitol (2). An investigation of the cyclization of diastereomeric oxiranyl radicals to achieve this goal was moderately successful with the diastereomer that would have led to epi-cyclophellitol undergoing cyclization. An alternative route to cyclophellitol from D-xylose employed Grubbs' ring closure metathesis and radical transformations to complete the synthesis.

  DOI：

  10.1021/jo981211d
• 作为产物：
  描述：

  (2S,3S)-3-[(1R,2S,3R)-1,2,3-Tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-butyl]-oxirane-2-carboxylic acid methyl ester 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 2.5h， 以82%的产率得到(2S,3S)-3-((1R,2S,3R)-1,2,3-Tris-benzyloxy-4-hydroxy-butyl)-oxirane-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Free Radical Studies and Solutions to the Synthesis of (+)-Cyclophellitol

  摘要：

  D-Xylose serves as a starting material for approaches to the synthesis of the glucosidase inhibitors, (+)-cyclophellitol (1) and (+)-epi-cyclophellitol (2). An investigation of the cyclization of diastereomeric oxiranyl radicals to achieve this goal was moderately successful with the diastereomer that would have led to epi-cyclophellitol undergoing cyclization. An alternative route to cyclophellitol from D-xylose employed Grubbs' ring closure metathesis and radical transformations to complete the synthesis.

  DOI：

  10.1021/jo981211d