5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose | 1224467-46-2

• 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-α-D-glycero-D-gluco-hepto-1,4-furanose
• 英文别名: (2S,3R)-3-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-azidopropane-1,2-diol
• CAS: 1224467-46-2
• 化学式: C₁₇H₂₃N₃O₆
• 分子量: 365.386
• InChiKey: DHJBMQOFIRBCRM-YTQIUSBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-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90%的产率得到5-benzyloxycarbonylamino-5-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
• 作为产物：
  描述：

  3-O-benzyl-5,6-anhydro-1,2-O-isopropylidene-α-D-glycero-L-ido-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88.2%的产率得到6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-L-glycero-L-ido-heptofuranose
  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

文献信息

• 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
  作者：Vrushali H. Jadhav、Omprakash P. Bande、Vedavati G. Puranik、Dilip D. Dhavale

  DOI：10.1016/j.tetasy.2010.01.007

  日期：2010.2

  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.