L-2,3-trans-3,4-cis-N-fluorenylmethoxycarbonyl-3,4-dihydroxy-3,4-O-isopropylidine-proline allyl ester | 221451-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: L-2,3-trans-3,4-cis-N-fluorenylmethoxycarbonyl-3,4-dihydroxy-3,4-O-isopropylidine-proline allyl ester
• 英文别名: 5-O-(9H-fluoren-9-ylmethyl) 4-O-prop-2-enyl (3aR,4S,6aS)-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4,5-dicarboxylate
• CAS: 221451-15-6
• 化学式: C₂₆H₂₇NO₆
• 分子量: 449.503
• InChiKey: CTGUIRUWTNTYLF-VABKMULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  L-2,3-trans-3,4-cis-N-fluorenylmethoxycarbonyl-3,4-dihydroxy-3,4-O-isopropylidine-proline allyl ester 在 二乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Synthesis of l-2,3-trans-3,4-cis-Dihydroxyproline Building Blocks for Peptide Synthesis

  摘要：

  L-2,3-trans-3,4-cis-N-Fluorenylmethoxycarbonyl-3,4-dihydroxy-3,4-O-isopropylidineproline (9) has been prepared from D-gulonolactone in nine steps and an overall yield of 22%. Compound 9 has been converted to its allyl ester 13. Compounds 9 and 13 were investigated as building blocks for the incorporation of dihydroxyproline into peptides, with compound 9 serving as a carboxyl component and compound 13 as a precursor to an amino component for peptide coupling reactions. Their utility was demonstrated by the synthesis of dipeptides 11 and 15.

  DOI：

  10.1021/jo982009d
• 作为产物：
  描述：

  3-溴丙烯 、 Caesium; (3aR,4S,6aS)-5-(9H-fluoren-9-ylmethoxycarbonyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carboxylate 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以97%的产率得到L-2,3-trans-3,4-cis-N-fluorenylmethoxycarbonyl-3,4-dihydroxy-3,4-O-isopropylidine-proline allyl ester
  参考文献：
  名称：

  Synthesis of l-2,3-trans-3,4-cis-Dihydroxyproline Building Blocks for Peptide Synthesis

  摘要：

  L-2,3-trans-3,4-cis-N-Fluorenylmethoxycarbonyl-3,4-dihydroxy-3,4-O-isopropylidineproline (9) has been prepared from D-gulonolactone in nine steps and an overall yield of 22%. Compound 9 has been converted to its allyl ester 13. Compounds 9 and 13 were investigated as building blocks for the incorporation of dihydroxyproline into peptides, with compound 9 serving as a carboxyl component and compound 13 as a precursor to an amino component for peptide coupling reactions. Their utility was demonstrated by the synthesis of dipeptides 11 and 15.

  DOI：

  10.1021/jo982009d