2-azido-4-phenyl-3-butene-1-yl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside | 312521-46-3

• 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: 2-azido-4-phenyl-3-butene-1-yl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-6-[(E)-2-azido-4-phenylbut-3-enoxy]-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 312521-46-3
• 化学式: C₄₄H₃₇N₃O₁₀
• 分子量: 767.792
• InChiKey: ZMMMZOPIFRDRER-HRAVUICTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  57
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-azido-4-phenyl-3-butene-1-yl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以88%的产率得到2-azido-4-phenyl-3-butene-1-yl β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiomerically enriched aminoalkenols and glycosides thereof

  摘要：

  1-t-Butoxycarbonylamido-3-pentene-1-ol 3 and 2-azido-4-phenyl-3-butene-1-ol 4 were enantiomerically enriched by enzymatic acetylation using various lipases and esterases (CHIRAZYM) to give acetylated compounds 5 and 7, respectively. Compound 3 gave the best results (E = 94) with Candida antarctica A lipase (CHIRAZYM L-5), whereas 4 could not be separated into the enantiomers with satisfactory E values. The absolute configurations were proven for both compounds via independently prepared derivatives. Both enantiomers of 5, as well as racemic 7, were N-deblocked and condensed with octonic acid derivatives 14 to give the corresponding C-glycosides 17 and 22 after deprotection of the intermediates in good overall yield. Compound 4 was similarly condensed with glucose imidate 11 to give the diastereomeric O-glycosides 13 after deprotection. The latter glycosides were prepared as precursors for the generation of the corresponding aldehydes as substrates for aldolase catalyzed reactions. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00294-9
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 147.0h， 生成 2-azido-4-phenyl-3-butene-1-yl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiomerically enriched aminoalkenols and glycosides thereof

  摘要：

  1-t-Butoxycarbonylamido-3-pentene-1-ol 3 and 2-azido-4-phenyl-3-butene-1-ol 4 were enantiomerically enriched by enzymatic acetylation using various lipases and esterases (CHIRAZYM) to give acetylated compounds 5 and 7, respectively. Compound 3 gave the best results (E = 94) with Candida antarctica A lipase (CHIRAZYM L-5), whereas 4 could not be separated into the enantiomers with satisfactory E values. The absolute configurations were proven for both compounds via independently prepared derivatives. Both enantiomers of 5, as well as racemic 7, were N-deblocked and condensed with octonic acid derivatives 14 to give the corresponding C-glycosides 17 and 22 after deprotection of the intermediates in good overall yield. Compound 4 was similarly condensed with glucose imidate 11 to give the diastereomeric O-glycosides 13 after deprotection. The latter glycosides were prepared as precursors for the generation of the corresponding aldehydes as substrates for aldolase catalyzed reactions. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00294-9

文献信息

• Chemoenzymatic synthesis of enantiomerically enriched aminoalkenols and glycosides thereof
  作者：Thomas Ziegler、Claus Jurisch

  DOI：10.1016/s0957-4166(00)00294-9

  日期：2000.8

  1-t-Butoxycarbonylamido-3-pentene-1-ol 3 and 2-azido-4-phenyl-3-butene-1-ol 4 were enantiomerically enriched by enzymatic acetylation using various lipases and esterases (CHIRAZYM) to give acetylated compounds 5 and 7, respectively. Compound 3 gave the best results (E = 94) with Candida antarctica A lipase (CHIRAZYM L-5), whereas 4 could not be separated into the enantiomers with satisfactory E values. The absolute configurations were proven for both compounds via independently prepared derivatives. Both enantiomers of 5, as well as racemic 7, were N-deblocked and condensed with octonic acid derivatives 14 to give the corresponding C-glycosides 17 and 22 after deprotection of the intermediates in good overall yield. Compound 4 was similarly condensed with glucose imidate 11 to give the diastereomeric O-glycosides 13 after deprotection. The latter glycosides were prepared as precursors for the generation of the corresponding aldehydes as substrates for aldolase catalyzed reactions. (C) 2000 Published by Elsevier Science Ltd.