pentafluorophenyl 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoate | 312521-48-5

• 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: pentafluorophenyl 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoate
• 英文别名: (2,3,4,5,6-pentafluorophenyl) 2-[(2S,3S,4R,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]acetate
• CAS: 312521-48-5
• 化学式: C₂₂H₂₁F₅O₁₁
• 分子量: 556.394
• InChiKey: NYMPRZLYGCRVQS-HZKUATSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  pentafluorophenyl 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoate 在 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (2,3,4,5,6-pentafluorophenyl) (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[2-[(2S,3S,4R,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]acetyl]amino]hexanoate
  参考文献：
  名称：

  Preparation of glycosyl amino acids as building blocks for the combinatorial synthesis of neoglycoconjugates

  摘要：

  Several neoglycosyl amino acids possessing a sugar residue, a spacer and trifunctional amino acid moiety were synthesized both in solution and solid phase by activating the carboxylic group as its pentafluorophenyl ester for condensation. The methodology is useful for application in combinatorial syntheses of neoglycoconjugates as potential mimics for oligosaccharides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00212-4
• 作为产物：
  描述：

  2-desoxy-3,7-anhydro-4,5,6,8-tetra-O-acetyl-D-glucooctonic acid 、 五氟苯酚 在 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以91%的产率得到pentafluorophenyl 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoate
  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