(2S,3S,4S)-3,4-bis-(tert-butyldimethylsilyloxy)-1-fluorenylmethoxycarbonyl-2-formylpyrrolidine | 443127-42-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S,3S,4S)-3,4-bis-(tert-butyldimethylsilyloxy)-1-fluorenylmethoxycarbonyl-2-formylpyrrolidine
• 英文别名: 9H-fluoren-9-ylmethyl (2S,3S,4S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-2-formylpyrrolidine-1-carboxylate
• CAS: 443127-42-2
• 化学式: C₃₂H₄₇NO₅Si₂
• 分子量: 581.9
• InChiKey: VUXLYNWUBKWMNI-ULNSLHSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-3,4-bis-(tert-butyldimethylsilyloxy)-1-fluorenylmethoxycarbonyl-2-formylpyrrolidine 在 sodium chlorite 、 potassium dihydrogenphosphate 、 环己烯 作用下， 以 叔丁醇 为溶剂， 反应 4.0h， 以93%的产率得到L-2,3-cis-3,4-trans-N-fluorenylmethoxycarbonyl-3,4-dihydroxy-3,4-di-O-tert-butyldimethylsilyl-proline
  参考文献：
  名称：

  Toward a General Strategy for the Synthesis of 3,4-Dihydroxyprolines from Pentose Sugars

  摘要：

  A general strategy is proposed, wherein a pentose sugar gamma-lactone can be converted, via a series of nine reactions, to a 3,4-dihydroxyproline, suitably protected for use in peptide synthesis. Thus, D-ribonolactone (6) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-D-2,3-cis-3,4-cis-proline (7) in 18.9% overall yield. Likewise, L-arabinonolactone (11) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-L-2,3-cis-3,4-trans-proline (36) in 13.7% overall yield and L-lyxonolactone (12) to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-L-2,3-trans-3,4-cis-proline (37) in 11.2% overall yield. These building blocks have also been fully deprotected to give the free amino acids. We believe that this series of reactions ought to be applicable to the synthesis of any of the eight stereoisomers of 3,4-dihydroxyproline, by judicious selection of the pentose starting material.

  DOI：

  10.1021/jo025538x
• 作为产物：
  描述：

  (2R,3S,4S)-3,4-bis-(tert-butyldimethylsilyloxy)-1-fluorenylmethoxycarbonyl-2-hydroxymethylpyrrolidine 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以96%的产率得到(2S,3S,4S)-3,4-bis-(tert-butyldimethylsilyloxy)-1-fluorenylmethoxycarbonyl-2-formylpyrrolidine
  参考文献：
  名称：

  Toward a General Strategy for the Synthesis of 3,4-Dihydroxyprolines from Pentose Sugars

  摘要：

  A general strategy is proposed, wherein a pentose sugar gamma-lactone can be converted, via a series of nine reactions, to a 3,4-dihydroxyproline, suitably protected for use in peptide synthesis. Thus, D-ribonolactone (6) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-D-2,3-cis-3,4-cis-proline (7) in 18.9% overall yield. Likewise, L-arabinonolactone (11) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-L-2,3-cis-3,4-trans-proline (36) in 13.7% overall yield and L-lyxonolactone (12) to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-L-2,3-trans-3,4-cis-proline (37) in 11.2% overall yield. These building blocks have also been fully deprotected to give the free amino acids. We believe that this series of reactions ought to be applicable to the synthesis of any of the eight stereoisomers of 3,4-dihydroxyproline, by judicious selection of the pentose starting material.

  DOI：

  10.1021/jo025538x

文献信息

• Toward a General Strategy for the Synthesis of 3,4-Dihydroxyprolines from Pentose Sugars
  作者：Carol M. Taylor、William D. Barker、Claudette A. Weir、Jae H. Park

  DOI：10.1021/jo025538x

  日期：2002.6.1

  A general strategy is proposed, wherein a pentose sugar gamma-lactone can be converted, via a series of nine reactions, to a 3,4-dihydroxyproline, suitably protected for use in peptide synthesis. Thus, D-ribonolactone (6) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-D-2,3-cis-3,4-cis-proline (7) in 18.9% overall yield. Likewise, L-arabinonolactone (11) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-L-2,3-cis-3,4-trans-proline (36) in 13.7% overall yield and L-lyxonolactone (12) to N-fluorenylmethoxycarbonyl-3,4-di-O-tent-butyldimethylsilyloxy-L-2,3-trans-3,4-cis-proline (37) in 11.2% overall yield. These building blocks have also been fully deprotected to give the free amino acids. We believe that this series of reactions ought to be applicable to the synthesis of any of the eight stereoisomers of 3,4-dihydroxyproline, by judicious selection of the pentose starting material.