(2S,3S,4S,5R,6R)-5-Acetoxy-3,4-bis-benzyloxy-6-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid | 193154-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S,3S,4S,5R,6R)-5-Acetoxy-3,4-bis-benzyloxy-6-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid
• CAS: 193154-29-9
• 化学式: C₃₇H₃₅NO₉
• 分子量: 637.686
• InChiKey: POEIQUIDDLZOGI-PYWJFMQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  129.62
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6R)-5-Acetoxy-3,4-bis-benzyloxy-6-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以77%的产率得到(1S,2S,3S,4R,5R)-4-Acetoxy-2,3-bis-benzyloxy-7-oxo-8-oxa-6-aza-bicyclo[3.2.1]octane-6-carboxylic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Backbone-Modified Phytoalexin Elicitor

  摘要：

  AbstractTwo suitably protected building blocks (11 and 33) for the preparation of amide‐linked heptaglucoside mimetic 2, an analogue of the naturally occurring phytoalexin elicitor 1a, were readily accessible by glycal chemistry. Sequential elongation of terminal glucuronide 21 with laminaribiosyl hemiaminal 33 and anomeric amine 11 by EDC/HOBt‐catalyzed condensation and two‐step conversion of the C6‐OTr moiety into the corresponding carboxylate function afforded homogeneous carbopeptoid 2 in high overall yield. It was found that replacement of the acetal linkages by the more rigid amide bonds destroys the phytoalexin‐elicitor activity.

  DOI：

  10.1002/chem.19970030614
• 作为产物：
  描述：

  2-O-acetyl-3,4-di-O-benzyl-6-O-trityl-β-D-glucopyranosylamine 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 四丁基氯化铵 、 碳酸氢钠 、 sodium carbonate 、 对甲苯磺酸 、 sodium chloride 、 potassium bromide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.25h， 生成 (2S,3S,4S,5R,6R)-5-Acetoxy-3,4-bis-benzyloxy-6-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Backbone-Modified Phytoalexin Elicitor

  摘要：

  AbstractTwo suitably protected building blocks (11 and 33) for the preparation of amide‐linked heptaglucoside mimetic 2, an analogue of the naturally occurring phytoalexin elicitor 1a, were readily accessible by glycal chemistry. Sequential elongation of terminal glucuronide 21 with laminaribiosyl hemiaminal 33 and anomeric amine 11 by EDC/HOBt‐catalyzed condensation and two‐step conversion of the C6‐OTr moiety into the corresponding carboxylate function afforded homogeneous carbopeptoid 2 in high overall yield. It was found that replacement of the acetal linkages by the more rigid amide bonds destroys the phytoalexin‐elicitor activity.

  DOI：

  10.1002/chem.19970030614