(R)-1-((2R,5S)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-ethane-1,2-diol | 141039-64-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (R)-1-((2R,5S)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-ethane-1,2-diol
• 英文别名: (1R)-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]ethane-1,2-diol
• CAS: 141039-64-7
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: BMPLPSJMCRWTFP-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.12
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.92
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  环己酮二甲缩酮 、 (R)-1-((2R,5S)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-ethane-1,2-diol 在 对甲苯磺酸 作用下， 生成 [(2S,5R)-(R)-5-(1,4-Dioxa-spiro[4.5]dec-2-yl)-tetrahydro-furan-2-yl]-methanol
  参考文献：
  名称：

  Development of tetrahydrofuran chiral synthons by enzymatic approach: Improved synthesis of a strong agonist of platelet activating factor

  摘要：

  Bicyclic meso diester 7 was found to undergo enantioselective hydrolysis with PLE (pig liver esterase) generating the chiral monoester 8 in excellent yield with high enantiomeric excess. The chiral monoester 8 was successfully utilized in the improved synthesis of 1R-cis-THF derivative (1), a strong agonist of PAF which we previously developed.

  DOI：

  10.1016/s0040-4039(00)91866-5
• 作为产物：
  描述：

  (2S,5R)-5-((S)-tert-Butoxycarbonyl-hydroxy-methyl)-tetrahydro-furan-2-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 生成 (R)-1-((2R,5S)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-ethane-1,2-diol
  参考文献：
  名称：

  Development of tetrahydrofuran chiral synthons by enzymatic approach: Improved synthesis of a strong agonist of platelet activating factor

  摘要：

  Bicyclic meso diester 7 was found to undergo enantioselective hydrolysis with PLE (pig liver esterase) generating the chiral monoester 8 in excellent yield with high enantiomeric excess. The chiral monoester 8 was successfully utilized in the improved synthesis of 1R-cis-THF derivative (1), a strong agonist of PAF which we previously developed.

  DOI：

  10.1016/s0040-4039(00)91866-5