(R)-6-O-benzyloxymethyl-4-hydroxycyclopent-2-enone | 94530-20-8

• 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: (R)-6-O-benzyloxymethyl-4-hydroxycyclopent-2-enone
• 英文别名: (R)-4-hydroxy-2-benzyloxymethylcyclopent-2-en-1-one；(4R)-4-hydroxy-2-(phenylmethoxymethyl)cyclopent-2-en-1-one
• CAS: 94530-20-8
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: FVWQOKSVCAGLBH-LBPRGKRZSA-N

物化性质

• 沸点：
  381.8±42.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-6-O-benzyloxymethyl-4-hydroxycyclopent-2-enone 在 咪唑 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,4R)-2-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-cyclopent-2-enol
  参考文献：
  名称：

  Novel 3′-deoxy analogs of the anti-HBV agent entecavir: synthesis of enantiomers from a single chiral epoxide

  摘要：

  A synthesis of novel 3'-deoxy analogs of the anti-HBV agent entecavir (BMS-200475) was devised using regioselective ring opening of suitable cyclopentene epoxides as the key step. This versatile approach afforded access to an enantiomeric pair of carbocyclic nucleosides from a single chiral intermediate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.052
• 作为产物：
  描述：

  (1S,2S,5R)-2-Benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexan-3-one 在 aluminum oxide 作用下， 以 乙醚 为溶剂， 以92%的产率得到(R)-6-O-benzyloxymethyl-4-hydroxycyclopent-2-enone
  参考文献：
  名称：

  Novel 3′-deoxy analogs of the anti-HBV agent entecavir: synthesis of enantiomers from a single chiral epoxide

  摘要：

  A synthesis of novel 3'-deoxy analogs of the anti-HBV agent entecavir (BMS-200475) was devised using regioselective ring opening of suitable cyclopentene epoxides as the key step. This versatile approach afforded access to an enantiomeric pair of carbocyclic nucleosides from a single chiral intermediate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.052

文献信息

• Synthesis of (R)-4-hydroxy-2-benzyloxymethylcyclopent-2-en-1-one from D-glucose via palladium(0)-catalysed rearrangement of a vinylic epoxide intermediate
  作者：Sa�d Achab、Jean-Pierre Cosson、Bhupesh C. Das

  DOI：10.1039/c39840001040

  日期：——

  transformation of D-glucose into (R)-4-hydroxy-2-benzyloxymethylcyclopent-2-en-1-one (3), a potential chiral synthon for the antibiotic (–)-pentenomycin I (4), has been achieved via the intramolecualr aldolisation–dehydration of the 2-hydroxy-4-oxo-aldehyde (9) which was obtained by two different routs, one of them involving palladium(0)-catalysed rearrangement of a vinylic epoxid intermediate.

  已实现将D-葡萄糖转化为（R）-4-羟基-2-苄氧基甲基环戊-2-en-1-one（3），它是抗生素（-）-喷新霉素I的潜在手性合成子（4）。通过分子内醛醇缩合-2-羟基-4-氧代醛的脱水反应（9），这是由两种不同的途径获得的，其中之一涉及钯（0）催化的乙烯基环氧中间体的重排。
• Achab, Said; Das, Bhupesh C., Journal of the Chemical Society. Perkin transactions I, 1990, # 11, p. 2863 - 2873
  作者：Achab, Said、Das, Bhupesh C.

  DOI：——

  日期：——
• ACHAB, SAID;DAS, BHUPESH C., J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N1, C. 2863-2873
  作者：ACHAB, SAID、DAS, BHUPESH C.

  DOI：——

  日期：——
• ACHAB, SAID;COSSON, J. -P.;DAS, B. C., J. CHEM. SOC. CHEM. COMMUN., 1984, N 15, 1040-1041
  作者：ACHAB, SAID、COSSON, J. -P.、DAS, B. C.

  DOI：——

  日期：——