(+/-)-(1RS,2RS,4SR,5SR,6SR)-5-exo,6-exo-(isopropylidenedioxy)-7-oxabicyclo<2.2.1>heptan-2-endo-ol | 114370-31-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-(1RS,2RS,4SR,5SR,6SR)-5-exo,6-exo-(isopropylidenedioxy)-7-oxabicyclo<2.2.1>heptan-2-endo-ol
• 英文别名: (1RS,2RS,6SR,7SR,8RS)-4,4-dimethyl-3,5,10-trioxatricyclo<5,2,1,0^2,ς> decan-8-ol；(1S,2S,6R,7R,8S)-4,4-dimethyl-3,5,10-trioxatricyclo[5.2.1.02,6]decan-8-ol
• CAS: 114370-31-9；114420-81-4
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: DSAOCOJLHAFSBK-YOWKYNACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.04
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  Butyric acid (1R,2R,4R,5S,6R)-5,6-dihydroxy-7-oxa-bicyclo[2.2.1]hept-2-yl ester 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 (+/-)-(1RS,2RS,4SR,5SR,6SR)-5-exo,6-exo-(isopropylidenedioxy)-7-oxabicyclo<2.2.1>heptan-2-endo-ol
  参考文献：
  名称：

  酶法制备旋光的7-氧杂双环[2.2.1]庚烷衍生物

  摘要：

  的酶拆分内-7-氧杂二环使用的脂肪酶从[2.2.1]庚-2-基丁酸酯3和5 Candida cylindracea的导致光学纯双环醇和酯是用于生物活性化合物的合成中的重要中间体。

  DOI：

  10.1016/s0040-4020(01)85830-0

文献信息

• Reductive Oxa Ring Opening of 7-Oxabicyclo[2.2.1]heptan-2-ones. Synthesis of C-.alpha.-Galactosides of Carbapentopyranoses
  作者：Janine Cossy、Jean-Luc Ranaivosata、Veronique Bellosta、Jacek Ancerewicz、Rafael Ferritto、Pierre Vogel

  DOI：10.1021/jo00131a007

  日期：1995.12

  Photoinduced electron transfer from Et(3)N to 7-oxabicyclo[2.2.1]heptan-2-ones can generate the corresponding 3-hydroxycyclohexanone derivatives. The method has been applied to the synthesis of C-alpha-D-galactopyranosides of carbapentopyranoses. Radical alpha-D-galactosidation of (+/-)-(1RS,4RS,5RS, 6RS)-6-endo-methoxy-3-methylidene-5-exo-(phenylseleno)-7-oxabicyclo[2.2.l]hept-2-one ((+)-51) followed by seleno-Pummerer rearrangement and reduction with Bu(3)SnH gave (+)- (1R,2S,3S,4R,6R)-((+)-58) and (+)-(1S,2R,3R,4S,6S)-3-endo-methoxy-5-oxo-6-endo-[(2',3',4',6'-tetra-0-acetyl-alpha-D-galactopyranosyl)methyl]-7-oxabicyclo[2.2.1]hept-2-endo-yl acetate ((+)-59), which were separated by column chromatography. Irradiation (254 nn) in the presence of Et(3)N gave (+)-(1S,2R,3R,6R)-((+)-60) and (+)-(1R,2S,3S,6S)-2-hydroxy-6-methoxy-4-oxo-3-[(2',3',4',6'-tetra-0-acetyl-alpha-D-galactopyranosyl)methyl]cyclohexyl acetate (+)-61, respectively. NaBH4 reduction and acetylation provided (+)-(1S,2S,3R,4R,5R)-((+)-62) and (+)-(1R,2R,3S,4S,5S)-5-methoxy-2-[(2',3',4',6'-tetra-0-acetyl-alpha-D-galactopyranosyl)methyl]cyclohexa-1,3,4-triyl triacetate ((+)-64).