(+)-(1S,2S)-dihydroxy-(3S,4S)-diacetoxycyclohex-5-ene | 193817-09-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(1S,2S)-dihydroxy-(3S,4S)-diacetoxycyclohex-5-ene
• 英文别名: [(1S,4S,5S,6R)-6-acetyloxy-4,5-dihydroxycyclohex-2-en-1-yl] acetate
• CAS: 193817-09-3
• 化学式: C₁₀H₁₄O₆
• 分子量: 230.218
• InChiKey: QNIDVYWZVDMFEA-XKNYDFJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1,2-diacetoxycyclohexa-3,5-diene 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (+)-(1S,2S)-dihydroxy-(3S,4S)-diacetoxycyclohex-5-ene
  参考文献：
  名称：

  Chemoenzymatic preparation of enantiopure partial esters of conduritol E

  摘要：

  Two partial esters of conduritol E, namely (2R)-hydroxy-(1R,3R,4R)-triacetoxycyclohex-5-ene and (1S,2S)-dihydroxy-(3S,4S)-diacetoxycyclohex-5-ene, have been prepared in high chemical and optical yields from 'benzene cis-glycol' diacetate via OsO4 catalysed dihydroxylation followed by enantioselective esterification of the resulting conduritol E diacetate in the presence of Mucor miehei lipase. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00233-4