methyl 2,4-anhydro-3-azido-3-deoxy-5-O-benzyl-L-rhamnonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2,4-anhydro-3-azido-3-deoxy-5-O-benzyl-L-rhamnonate
• 英文别名: methyl (2R,3R,4R)-3-azido-4-[(1S)-1-phenylmethoxyethyl]oxetane-2-carboxylate
• 化学式: C₁₄H₁₇N₃O₄
• 分子量: 291.307
• InChiKey: AJTSGRURDOLMSZ-ZBAXXZLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-rhamnopyranose 在 三乙基硅烷 、 sodium azide 、 溴 、 氧化汞红 、 potassium carbonate 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 2.0h， 生成 methyl 2,4-anhydro-3-azido-3-deoxy-5-O-benzyl-L-rhamnonate
  参考文献：
  名称：

  cis- and trans-3-Azido-oxetane-2-carboxylate scaffolds: hexamers of oxetane cis-β-amino acids

  摘要：

  Efficient synthesis of both cis- and trans-3-azido-oxktane-2-carboxylates relies upon efficient nucleophilic displacements of 3-O-triflates of oxetanes by trifluoroacetate and azide. Such structures are scaffolds for incorporation of oxetane-beta-amino acids into oligomers; the synthesis of a series of protected beta-hexapeptides and the X-ray crystal structure of methyl 2,4-anhydro-6-deoxy-5-O-benzyl-L-altronate are reported. (C) 2001 Elsevier Science Ltd. AII rights reserved.

  DOI：

  10.1016/s0040-4039(01)00660-8

文献信息

• cis- and trans-3-Azido-oxetane-2-carboxylate scaffolds: hexamers of oxetane cis-β-amino acids
  作者：Sarah F Barker、Donald Angus、Claude Taillefumier、Michael R Probert、David J Watkin、Mark P Watterson、Timothy D.W Claridge、Natasha L Hungerford、George W.J Fleet

  DOI：10.1016/s0040-4039(01)00660-8

  日期：2001.6

  Efficient synthesis of both cis- and trans-3-azido-oxktane-2-carboxylates relies upon efficient nucleophilic displacements of 3-O-triflates of oxetanes by trifluoroacetate and azide. Such structures are scaffolds for incorporation of oxetane-beta-amino acids into oligomers; the synthesis of a series of protected beta-hexapeptides and the X-ray crystal structure of methyl 2,4-anhydro-6-deoxy-5-O-benzyl-L-altronate are reported. (C) 2001 Elsevier Science Ltd. AII rights reserved.
• Oxetane cis- and trans-β-amino-acid scaffolds from l-rhamnose by efficient SN2 reactions in oxetane rings; pseudoenantiomeric analogues of the antibiotic oxetin
  作者：Stephen W. Johnson、Sarah F. Jenkinson (née Barker)、Donald Angus、John H. Jones、George W.J. Fleet、Claude Taillefumier

  DOI：10.1016/j.tetasy.2004.07.032

  日期：2004.9

  An efficient multigram ring contraction of a 1,4-lactone 2-O-triflate derived from L-rhamnose-with retention of configuration in the ring closure-is the key step in the preparation of a series of oxetanes, which are pseudoenantiomeric analogues of the naturally occurring antibiotic oxetin, an oxetane cis-beta-amino acid. Subsequent nucleophilic displacements of the corresponding triflates by azide proceed in consistently excellent yields, without any elimination, to provide syntheses of scaffolds for analogues of the antibiotic. (C) 2004 Elsevier Ltd. All rights reserved.