trans-N-tert-butyloxycarbonyl-4-hydroxy-4-[2,3,5-tribenzyl-α-L-arabinofuranosyl]-L-proline allyl ester | 1253376-03-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: trans-N-tert-butyloxycarbonyl-4-hydroxy-4-[2,3,5-tribenzyl-α-L-arabinofuranosyl]-L-proline allyl ester
• CAS: 1253376-03-2
• 化学式: C₃₉H₄₇NO₉
• 分子量: 673.803
• InChiKey: TZPJQKPIFSEJKK-ZTJZJMSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.22
• 重原子数：
  49.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  101.99
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  (4R)-hydroxypyrrolidine-1,(2S)-dicarboxylic acid 2-allyl ester 1-tert-butyl ester 、 4-methylphenyl 2,3,5-tri-O-benzyl-1-thio-L-arabinofuranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 以50%的产率得到trans-N-tert-butyloxycarbonyl-4-hydroxy-4-[2,3,5-tribenzyl-β-L-arabinofuranosyl]-L-proline allyl ester
  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