2,5-anhydro-6-O-benzoyl-3,4-O-isopropylidene-D-allose | 39037-13-3

• 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: 2,5-anhydro-6-O-benzoyl-3,4-O-isopropylidene-D-allose
• 英文别名: [(3aR,4R,6R,6aR)-4-formyl-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl benzoate
• CAS: 39037-13-3
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: OPLURXCPJMSWGV-RFQIPJPRSA-N

物化性质

• 沸点：
  425.0±45.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2S,3S,4R,5R)-2-acetoxymethyl-5-(hydroxymethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran 在 吡啶 、 sodium acetate 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 2,5-anhydro-6-O-benzoyl-3,4-O-isopropylidene-D-allose
  参考文献：
  名称：

  Pseudomonas fluorescens lipase-catalyzed asymmetric hydrolysis and transesterification of meso-2,5-bis(acetoxymethyl)- and bis(hydroxymethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran

  摘要：

  Pseudomonas fluorescens lipase (PFL)-catalyzed asymmetric hydrolysis of meso-2,5-bis(acetoxymethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran 3 afforded the optically active monoacetate (-)-7 of high enantiomeric excess (92% ee) in 94% yield. Transesterification of meso-bis(hydroxymethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran 6 using PFL in vinyl acetate gave the monoacetate (+)-7 of 69% ee in low yield (15%). The absolute configuration of (-)-7 was determined to be 2S,3S,4R,5R, by chemical correlation with D-allose 10. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00369-8

文献信息

• Pseudomonas fluorescens lipase-catalyzed asymmetric hydrolysis and transesterification of meso-2,5-bis(acetoxymethyl)- and bis(hydroxymethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran
  作者：Kenji Matsuo、Masakazu Tanaka、Kiyoshi Sakai、Hiroshi Suemune

  DOI：10.1016/s0957-4166(97)00369-8

  日期：1997.9

  Pseudomonas fluorescens lipase (PFL)-catalyzed asymmetric hydrolysis of meso-2,5-bis(acetoxymethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran 3 afforded the optically active monoacetate (-)-7 of high enantiomeric excess (92% ee) in 94% yield. Transesterification of meso-bis(hydroxymethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran 6 using PFL in vinyl acetate gave the monoacetate (+)-7 of 69% ee in low yield (15%). The absolute configuration of (-)-7 was determined to be 2S,3S,4R,5R, by chemical correlation with D-allose 10. (C) 1997 Published by Elsevier Science Ltd.