3,4,6-tri-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-carbmethoxyazidomethyl-β-D-glucopyranosyl azide | 1609184-87-3

• 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: 3,4,6-tri-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-carbmethoxyazidomethyl-β-D-glucopyranosyl azide
• CAS: 1609184-87-3
• 化学式: C₂₇H₅₆N₆O₆Si₃
• 分子量: 645.035
• InChiKey: JIXDQOITHXQHIE-YTAOHXRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.29
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  160.74
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-carbmethoxyazidomethyl-β-D-glucopyranosyl azide 在 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以66%的产率得到(3S)-3-amino-[3,4,6-tri-O-(tert-butyldimethylsilyl)-1,2-dideoxy-α-D-glucopyranoso][2,3-b]-pyrrolidin-2-one
  参考文献：
  名称：

  Novel synthesis of carbohydrate fused α-amino γ-lactams and glycopeptides by NIS mediated ring opening of donor–acceptor substituted cyclopropanes

  摘要：

  alpha-Amino gamma-lactams have been synthesized from carbohydrate derived cyclopropanecarboxylates using N-iodosuccinimide (NIS) and NaN3. Cyclopropane ring opening with NIS and NaN3 in different solvents has been studied. Reductive cyclization of the intermediate di-azides leads to the carbohydrate fused alpha-amino gamma-lactam and gamma-lactams. Additionally, the methodology has been successfully extended to the synthesis of a glycopeptide. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.02.022
• 作为产物：
  描述：

  三-O-(叔丁基二甲基甲硅烷基)-D-葡萄烯糖 在 dirhodium tetraacetate 、 N-碘代丁二酰亚胺 、 sodium azide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 40.0h， 生成 3,4,6-tri-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-carbmethoxyazidomethyl-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Novel synthesis of carbohydrate fused α-amino γ-lactams and glycopeptides by NIS mediated ring opening of donor–acceptor substituted cyclopropanes

  摘要：

  alpha-Amino gamma-lactams have been synthesized from carbohydrate derived cyclopropanecarboxylates using N-iodosuccinimide (NIS) and NaN3. Cyclopropane ring opening with NIS and NaN3 in different solvents has been studied. Reductive cyclization of the intermediate di-azides leads to the carbohydrate fused alpha-amino gamma-lactam and gamma-lactams. Additionally, the methodology has been successfully extended to the synthesis of a glycopeptide. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.02.022