3-benzyloxycarbonylamino-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose | 37073-89-5

• 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: 3-benzyloxycarbonylamino-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose
• 英文别名: benzyl N-[(3aR,5S,6R,6aR)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]carbamate
• CAS: 37073-89-5
• 化学式: C₁₇H₂₃NO₇
• 分子量: 353.372
• InChiKey: KFOAWHBZUSXXTL-KJWHEZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-benzyloxycarbonylamino-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose 在 Grubbs catalyst first generation 咪唑 、 碘 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.0h， 生成 benzyl (1R,2R,6R,8R)-4,4-dimethyl-3,5,7-trioxa-12-azatricyclo[6.4.0.02,6]dodec-9-ene-12-carboxylate
  参考文献：
  名称：

  A general strategy for the stereoselective synthesis of l-1-deoxyallonojirimycin and d-1-deoxygulonojirimycin

  摘要：

  A general strategy for the synthesis of deoxyazasugars from D-glucose is described. Ring-closing metathesis and stereoselective dihydroxylation reactions were used as key steps. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.110
• 作为产物：
  描述：

  3-azido-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 3-benzyloxycarbonylamino-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose
  参考文献：
  名称：

  A general strategy for the stereoselective synthesis of l-1-deoxyallonojirimycin and d-1-deoxygulonojirimycin

  摘要：

  A general strategy for the synthesis of deoxyazasugars from D-glucose is described. Ring-closing metathesis and stereoselective dihydroxylation reactions were used as key steps. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.110

文献信息

• Synthesis, conformational study, glycosidase inhibitory activity and molecular docking studies of dihydroxylated 4- and 5-amino-iminosugars
  作者：Vijay M. Kasture、Navnath B. Kalamkar、Roopa J. Nair、Rakesh S. Joshi、Sushma G. Sabharwal、Dilip D. Dhavale

  DOI：10.1016/j.carres.2015.03.004

  日期：2015.5

  An efficient methodology for the synthesis of new amino iminosugars 6a, 7a and 8, starting from D-glucose, is reported. The conformational study using (1)H NMR data showed that the amino iminosugar 6a exists in the (2)C5 while; the 7a and 8 exist in the (5)C2 conformation. The inhibition activities with different glycosidases showed that 6a and 7a are poor glycosidase inhibitors. However, amino iminosugar

  报道了一种从D-葡萄糖开始合成新的氨基亚氨基糖6a，7a和8的有效方法。使用（1）H NMR数据进行的构象研究表明，氨基亚氨基糖6a存在于（2）C5中；7a和8以（5）C2构象存在。不同糖苷酶的抑制活性表明6a和7a是不良的糖苷酶抑制剂。然而，氨基亚氨基糖8显示出对β-半乳糖苷酶的选择性抑制（IC50 = 43μM，Ki = 153μM）。这些结果通过分子对接研究得到证实。
• A general strategy for the stereoselective synthesis of l-1-deoxyallonojirimycin and d-1-deoxygulonojirimycin
  作者：Subhash Ghosh、J. Shashidhar、Samit Kumar Dutta

  DOI：10.1016/j.tetlet.2006.06.110

  日期：2006.8

  A general strategy for the synthesis of deoxyazasugars from D-glucose is described. Ring-closing metathesis and stereoselective dihydroxylation reactions were used as key steps. (c) 2006 Elsevier Ltd. All rights reserved.