(3aR,4R,6S,6aS)-tert-butyl 4,6-bis(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate | 726192-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3aR,4R,6S,6aS)-tert-butyl 4,6-bis(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate
• 英文别名: meso-(2S,3S,4R,5R)-N-(tert-butoxycarbonyl)-2,5-dihydroxymethyl-3,4-isopropylidenedioxypyrrolidine；tert-butyl (3aS,4S,6R,6aR)-4,6-bis(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 726192-22-9
• 化学式: C₁₄H₂₅NO₆
• 分子量: 303.356
• InChiKey: HNQZGPIFYBFOAY-DTIDVZRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  88.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,4R,6S,6aS)-tert-butyl 4,6-bis(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以100%的产率得到meso-(2S,3S,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine hydrochloride
  参考文献：
  名称：

  Synthesis of d- and l-2,3-trans-3,4-cis-4,5-trans-3,4-Dihydroxy-5-hydroxymethylproline and Tripeptides Containing Them

  摘要：

  Enantiomerically pure (-)-(1R,4R,5R,6S)- and (+)-(1S,4S,5S,6R)-7-(tert-butoxycarbonyl)-5,6-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]hept-2-one ((-)-3 and (+)-3) have been obtained from the Diels-Alder adduct of N-(tert-butoxycarbonyl)pyrrole and 2-bromo-1-(p-toluenesulfonyl)acetylene, including the Alexakis optical resolution of ketone ()-3 via formation of cyclic aminals with (1R,2R)diphenylethylenediamine. Compounds (-)-3 and (+)-3 were converted into D- and L-2,3-trans-3,4-cis-4,5-trans-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-isopropylidenedioxyprolines (-)-4 and (+)4, respectively. Applying the Boc and Fmoc strategies of peptide synthesis, these compounds were used to construct two tripeptides containing the D- or L-2,3-trans-3,4-cis-4,5-trans-3,4-dihydroxy-5-hydroxymethylproline.

  DOI：

  10.1021/jo049637h
• 作为产物：
  描述：

  [(3aR,4R,6S,6aS)-5-(tert-butoxycarbonyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-4,6-diyl]bis(methyl) diacetate 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 以95%的产率得到(3aR,4R,6S,6aS)-tert-butyl 4,6-bis(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate
  参考文献：
  名称：

  吡咯烷和吡咯啉衍生物的酶促脱对称

  摘要：

  各种的酶desymmetrization内消旋- ñ -Boc-2,5-顺式二取代的吡咯烷和吡咯啉化合物通过酯水解或酯交换提供高对映体过量的相应单酯。

  DOI：

  10.1016/j.tetasy.2008.05.022

文献信息

• Enzymatic desymmetrization of pyrrolidine and pyrroline derivatives
  作者：Robert Chênevert、Frédéric Jacques、Pascall Giguère、Mohammed Dasser

  DOI：10.1016/j.tetasy.2008.05.022

  日期：2008.6

  The enzymatic desymmetrization of various meso-N-Boc-2,5-cis-disubstituted pyrrolidines and pyrrolines compounds by ester hydrolysis or transesterification provided the corresponding monoesters in high enantiomeric excess.

  各种的酶desymmetrization内消旋- ñ -Boc-2,5-顺式二取代的吡咯烷和吡咯啉化合物通过酯水解或酯交换提供高对映体过量的相应单酯。
• Synthesis of <scp>d</scp>- and <scp>l</scp>-2,3-<i>trans</i>-3,4-<i>cis</i>-4,5-<i>trans</i>-3,4-Dihydroxy-5-hydroxymethylproline and Tripeptides Containing Them
  作者：Antonio J. Moreno-Vargas、Inmaculada Robina、Elena Petricci、Pierre Vogel

  DOI：10.1021/jo049637h

  日期：2004.6.1

  Enantiomerically pure (-)-(1R,4R,5R,6S)- and (+)-(1S,4S,5S,6R)-7-(tert-butoxycarbonyl)-5,6-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]hept-2-one ((-)-3 and (+)-3) have been obtained from the Diels-Alder adduct of N-(tert-butoxycarbonyl)pyrrole and 2-bromo-1-(p-toluenesulfonyl)acetylene, including the Alexakis optical resolution of ketone ()-3 via formation of cyclic aminals with (1R,2R)diphenylethylenediamine. Compounds (-)-3 and (+)-3 were converted into D- and L-2,3-trans-3,4-cis-4,5-trans-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-isopropylidenedioxyprolines (-)-4 and (+)4, respectively. Applying the Boc and Fmoc strategies of peptide synthesis, these compounds were used to construct two tripeptides containing the D- or L-2,3-trans-3,4-cis-4,5-trans-3,4-dihydroxy-5-hydroxymethylproline.