trans-N-tert-butyloxycarbonyl-4-hydroxy-4-[2,3,5-tribenzyl-β-L-arabinofuranosyl]-L-proline | 1253376-06-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans-N-tert-butyloxycarbonyl-4-hydroxy-4-[2,3,5-tribenzyl-β-L-arabinofuranosyl]-L-proline
• 英文别名: prop-2-enyl (2S,4R)-4-[(2S,3R,4S,5S)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]oxypyrrolidine-2-carboxylate
• CAS: 1253376-06-5
• 化学式: C₃₄H₃₉NO₇
• 分子量: 573.686
• InChiKey: JULJTGMBALGZBP-BOQDSQTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  trans-N-tert-butyloxycarbonyl-4-hydroxy-4-[2,3,5-tribenzyl-β-L-arabinofuranosyl]-L-proline 、 trans-4-hydroxy-4-[2,3,5-tribenzyl-β-L-arabinofuranosyl]-L-proline allyl ester 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 为溶剂， 以45 mg的产率得到prop-2-enyl (2S,4R)-4-[(2S,3R,4S,5S)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]oxy-1-[(2S,4R)-4-[(2S,3R,4S,5S)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]oxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Synthesis of a Dimer of β-(1,4)-l-Arabinosyl-(2S,4R)-4-hydroxyproline Inspired by Art v 1, the Major Allergen of Mugwort

  摘要：

  N alpha-tert-Butoxycarbonyl-L-trans-4-hydroxyproline allyl ester (Boc-Hyp-OAII) was glycosylated with 2,3,5-tri-O-benzyl-L-arabinose p-cresylthioglycoside in 60% yield with 4:1 beta:alpha stereoselectivity. Deprotection of N- and C-terminii independently gave a prolyl amine and prolyl carboxylate respectively that were coupled under standard conditions with 1-[bis-(dimethylamino)methylene]-1H-1,2,3-triazolo-[4,5,b]-pyridininium hexafluorophosphate 3-oxide (N-HATU) to give the dimer 1 in 46% yield. These results represent the first steps toward the production of homogeneous oligomers to determine the minimal epitope of the Art v 1 allergen.

  DOI：

  10.1021/ol102112z
• 作为产物：
  描述：

  trans-N-tert-butyloxycarbonyl-4-hydroxy-4-[2,3,5-tribenzyl-β-L-arabinofuranosyl]-L-proline allyl ester 在 N-甲基吗啉 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 trans-N-tert-butyloxycarbonyl-4-hydroxy-4-[2,3,5-tribenzyl-β-L-arabinofuranosyl]-L-proline
  参考文献：
  名称：

  Synthesis of a Dimer of β-(1,4)-l-Arabinosyl-(2S,4R)-4-hydroxyproline Inspired by Art v 1, the Major Allergen of Mugwort

  摘要：

  N alpha-tert-Butoxycarbonyl-L-trans-4-hydroxyproline allyl ester (Boc-Hyp-OAII) was glycosylated with 2,3,5-tri-O-benzyl-L-arabinose p-cresylthioglycoside in 60% yield with 4:1 beta:alpha stereoselectivity. Deprotection of N- and C-terminii independently gave a prolyl amine and prolyl carboxylate respectively that were coupled under standard conditions with 1-[bis-(dimethylamino)methylene]-1H-1,2,3-triazolo-[4,5,b]-pyridininium hexafluorophosphate 3-oxide (N-HATU) to give the dimer 1 in 46% yield. These results represent the first steps toward the production of homogeneous oligomers to determine the minimal epitope of the Art v 1 allergen.

  DOI：

  10.1021/ol102112z

文献信息

• Synthesis of a Dimer of β-(1,4)-<scp>l</scp>-Arabinosyl-(2<i>S</i>,4<i>R</i>)-4-hydroxyproline Inspired by Art v 1, the Major Allergen of Mugwort
  作者：Ning Xie、Carol M. Taylor

  DOI：10.1021/ol102112z

  日期：2010.11.5

  N alpha-tert-Butoxycarbonyl-L-trans-4-hydroxyproline allyl ester (Boc-Hyp-OAII) was glycosylated with 2,3,5-tri-O-benzyl-L-arabinose p-cresylthioglycoside in 60% yield with 4:1 beta:alpha stereoselectivity. Deprotection of N- and C-terminii independently gave a prolyl amine and prolyl carboxylate respectively that were coupled under standard conditions with 1-[bis-(dimethylamino)methylene]-1H-1,2,3-triazolo-[4,5,b]-pyridininium hexafluorophosphate 3-oxide (N-HATU) to give the dimer 1 in 46% yield. These results represent the first steps toward the production of homogeneous oligomers to determine the minimal epitope of the Art v 1 allergen.