methyl 2,4-anhydro-3-azido-5-O-benzyl-3-deoxy-D-arabinonate | 357400-98-7

• 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-5-O-benzyl-3-deoxy-D-arabinonate
• 英文别名: methyl (2S,3R,4S)-3-azido-4-(phenylmethoxymethyl)oxetane-2-carboxylate
• CAS: 357400-98-7
• 化学式: C₁₃H₁₅N₃O₄
• 分子量: 277.28
• InChiKey: SUNIXJKQMZHEOY-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,4-anhydro-3-azido-5-O-benzyl-3-deoxy-D-arabinonate 生成 methyl (2S,3R,4S)-3-[[(2S,3R,4S)-3-[[(2S,3R,4S)-3-[[(2S,3R,4S)-3-[[(2S,3R,4S)-3-[[(2S,3R,4S)-3-azido-4-(phenylmethoxymethyl)oxetane-2-carbonyl]amino]-4-(phenylmethoxymethyl)oxetane-2-carbonyl]amino]-4-(phenylmethoxymethyl)oxetane-2-carbonyl]amino]-4-(phenylmethoxymethyl)oxetane-2-carbonyl]amino]-4-(phenylmethoxymethyl)oxetane-2-carbonyl]amino]-4-(phenylmethoxymethyl)oxetane-2-carboxylate
  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
• 作为产物：
  描述：

  D-吡喃木糖 在 吡啶 、 三乙基硅烷 、 sodium azide 、 溴 、 potassium carbonate 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 methyl 2,4-anhydro-3-azido-5-O-benzyl-3-deoxy-D-arabinonate
  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

• Oxetane cis- and trans β-amino-acid scaffolds from d-xylose by efficient SN2 reactions in oxetane rings: methyl and hydroxymethyl analogues of the antibiotic oxetin, an oxetane β-amino-acid
  作者：Sarah F. Jenkinson (née Barker)、Timothy Harris、George W.J. Fleet

  DOI：10.1016/j.tetasy.2004.07.031

  日期：2004.9

  Highly regioselective reactions of a benzylidene-protected oxetane with (i) triethylsilane-trifluoroacetic acid and (ii) Hanessian-Hullar bromination provide efficient access to 3-hydroxyoxetane carboxylates in which only the C-3 OH is unprotected. Subsequent nucleophilic displacements of the corresponding triflates by azide proceeds in consistently excellent yields without any elimination to provide syntheses of scaffolds for a range of methyl and hydroxymethyl analogues of the antibiotic oxetin, a naturally occurring oxetane cis-beta-amino acid. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.