5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-L-glycero-L-ido-hepto-1,4-furanose | 1224467-47-3

• 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: 5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-L-glycero-L-ido-hepto-1,4-furanose
• CAS: 1224467-47-3
• 化学式: C₁₇H₂₃N₃O₆
• 分子量: 365.386
• InChiKey: DHJBMQOFIRBCRM-RWHKXBQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  126.14
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-L-glycero-L-ido-hepto-1,4-furanose 、 氯甲酸苄酯 在 palladium 10% on activated carbon 、 甲酸铵 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 19.0h， 以92%的产率得到5-(N-benzoxycarbonyl)amino-3,6,7-trihydroxy-5-deoxy-1,2-O-isopropylidene-β-L-glycero-L-ido-hepto-1,4-furanose
  参考文献：
  名称：

  Synthesis of azepane and nojirimycin iminosugars: the Sharpless asymmetric epoxidation of d-glucose-derived allyl alcohol and highly regioselective epoxide ring opening using sodium azide

  摘要：

  The Sharp less asymmetric epoxidation of D-glucose-derived ally! alcohol 4 afforded alpha- and beta-epoxides 5a and 5b in high stereoselectivity. The epoxide ring opening in 5a/5b was studied with different nucleophilic azido reagents, under various reaction conditions, and was found to be highly regioselective to give the preferential formation of 6-azido diol 6a/6b over 5-azido-diol 7a/7b. The 6-azido diol 6a/6b and 5-azido dial 7a/7b thus obtained were converted to the corresponding seven- and six-membered iminosugar, namely, azepane 1a/1b and 1-deoxy-nojirimycin 2a/2b. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.01.007
• 作为产物：
  描述：

  3-O-benzyl-5,6-anhydro-1,2-O-isopropylidene-β-L-glycero-D-gluco-hepto-1,4-furanose 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以80.9%的产率得到6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose
  参考文献：
  名称：

  Synthesis of azepane and nojirimycin iminosugars: the Sharpless asymmetric epoxidation of d-glucose-derived allyl alcohol and highly regioselective epoxide ring opening using sodium azide

  摘要：

  The Sharp less asymmetric epoxidation of D-glucose-derived ally! alcohol 4 afforded alpha- and beta-epoxides 5a and 5b in high stereoselectivity. The epoxide ring opening in 5a/5b was studied with different nucleophilic azido reagents, under various reaction conditions, and was found to be highly regioselective to give the preferential formation of 6-azido diol 6a/6b over 5-azido-diol 7a/7b. The 6-azido diol 6a/6b and 5-azido dial 7a/7b thus obtained were converted to the corresponding seven- and six-membered iminosugar, namely, azepane 1a/1b and 1-deoxy-nojirimycin 2a/2b. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.01.007