Acetic acid (1R,2S,3R,4S,5R,6R)-3-acetoxy-4,5-dihydroxy-7-oxa-bicyclo[4.1.0]hept-2-yl ester | 214852-46-7

• 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 (1R,2S,3R,4S,5R,6R)-3-acetoxy-4,5-dihydroxy-7-oxa-bicyclo[4.1.0]hept-2-yl ester
• CAS: 214852-46-7
• 化学式: C₁₀H₁₄O₇
• 分子量: 246.217
• InChiKey: WKRLBOVBRXMZGV-IHICSVBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.65
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  105.59
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (1R,2S,3R,4S,5R,6R)-3-acetoxy-4,5-dihydroxy-7-oxa-bicyclo[4.1.0]hept-2-yl ester 在 palladium on activated charcoal sodium azide 、 氢气 、 氯化铵 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成
  参考文献：
  名称：

  Convenient access to both enantiomers of new azido- and aminoinositols via a chemoenzymatic route

  摘要：

  1,2-diacetylconduritol E, (+/-)-1, through complementary use of Mucor miehei (Lipozyme(R) IM) and Candida cylindracea lipases, affords (1S)-1,2-diacetylconduritol E, (+)-1, (1R)-1,2-diacetylconduritol E, (-)-1, (1S)-1,2,4-triacetylconduritol E, (+)-2, (1R)-1,2,4-triacetylconduritol E, (-)-2, with high enantiomeric excesses and chemical yields. Following two different methods, diester (+)-1 has been transformed into azidoinositol (-)-4 to give 1L-4-amino-4-deoxy-chiro-inositol, whereas triester (-)-2 furnished the azidoinositol (+)-13, easily converted into 1L-4-amino-4-deoxy-myo-inositol. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00271-7
• 作为产物：
  描述：

  (+)-(1S,2S)-dihydroxy-(3S,4S)-diacetoxycyclohex-5-ene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以86%的产率得到Acetic acid (1R,2S,3R,4S,5R,6R)-3-acetoxy-4,5-dihydroxy-7-oxa-bicyclo[4.1.0]hept-2-yl ester
  参考文献：
  名称：

  Convenient access to both enantiomers of new azido- and aminoinositols via a chemoenzymatic route

  摘要：

  1,2-diacetylconduritol E, (+/-)-1, through complementary use of Mucor miehei (Lipozyme(R) IM) and Candida cylindracea lipases, affords (1S)-1,2-diacetylconduritol E, (+)-1, (1R)-1,2-diacetylconduritol E, (-)-1, (1S)-1,2,4-triacetylconduritol E, (+)-2, (1R)-1,2,4-triacetylconduritol E, (-)-2, with high enantiomeric excesses and chemical yields. Following two different methods, diester (+)-1 has been transformed into azidoinositol (-)-4 to give 1L-4-amino-4-deoxy-chiro-inositol, whereas triester (-)-2 furnished the azidoinositol (+)-13, easily converted into 1L-4-amino-4-deoxy-myo-inositol. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00271-7