2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-L-lyxono-γ-lactone | 443127-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-L-lyxono-γ-lactone
• 英文别名: (3R,4R,5S)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-(trityloxymethyl)oxolan-2-one
• CAS: 443127-30-8
• 化学式: C₃₆H₅₀O₅Si₂
• 分子量: 618.961
• InChiKey: IYFQYKFILOWLNJ-DCMFLLSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-L-lyxono-γ-lactone 在 吡啶 、 4-二甲氨基吡啶 、 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 32.0h， 生成 2,3-bis-O-tert-butyldimethylsilyl-1,4-bis-O-methanesulfonyl-5-O-triphenylmethyl-L-lyxitol
  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：

  L-来苏糖酸-1,4-内酯 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 2,3-bis-O-tert-butyldimethylsilyl-5-O-triphenylmethyl-L-lyxono-γ-lactone
  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.