methyl 2,4-anhydro-3-azido-5-O-tertbutyldiphenylsilyl-3-deoxy-D-lyxonate | 787572-23-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: methyl 2,4-anhydro-3-azido-5-O-tertbutyldiphenylsilyl-3-deoxy-D-lyxonate
• 英文别名: methyl (2S,3S,4S)-3-azido-4-[[tert-butyl(diphenyl)silyl]oxymethyl]oxetane-2-carboxylate
• CAS: 787572-23-0
• 化学式: C₂₂H₂₇N₃O₄Si
• 分子量: 425.56
• InChiKey: VMSKIKMHCSQXMN-AABGKKOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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-tertbutyldiphenylsilyl-3-deoxy-D-lyxonate 在 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以76%的产率得到methyl 2,4-anhydro-3-azido-3-deoxy-D-lyxonate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2004.07.031
• 作为产物：
  描述：

  D-木糖酸-gamma-内酯 在 吡啶 、 咪唑 、 盐酸 、 sodium azide 、 氧化汞红 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 47.25h， 生成 methyl 2,4-anhydro-3-azido-5-O-tertbutyldiphenylsilyl-3-deoxy-D-lyxonate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2004.07.031

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.