benzyl N-[(3aR,5R,6R,6aR)-5-ethenyl-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]carbamate | 910479-44-6

• 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: benzyl N-[(3aR,5R,6R,6aR)-5-ethenyl-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]carbamate
• CAS: 910479-44-6
• 化学式: C₁₇H₂₁NO₅
• 分子量: 319.357
• InChiKey: AZXHEKKHXMGUBJ-KBUPBQIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl N-[(3aR,5R,6R,6aR)-5-ethenyl-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]carbamate 在 Grubbs catalyst first generation sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 、 sodium hydride 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 38.0h， 生成 benzyl (1R,2R,6R,8S,9R,10R)-9,10-dihydroxy-4,4-dimethyl-3,5,7-trioxa-12-azatricyclo[6.4.0.02,6]dodecane-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 咪唑 、 氢气 、 碘 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成 benzyl N-[(3aR,5R,6R,6aR)-5-ethenyl-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]carbamate
  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 and Glycosidase Inhibition Study of 2-<i>C</i>-Hydroxymethyl- and 6-<i>C</i>-Hydroxymethyl-Branched Piperidines from<scp>D</scp>-Glucose Using Ene-Yne Metathesis as a Key Step
  作者：Asadulla Mallick、Yashwant D. Vankar

  DOI：10.1002/ejoc.201402142

  日期：2014.7

  were synthesized from readily available 1,2:5,6-di-O-isopropylidene-α-glucofuranose through an ene-yne metathesis as the key step. The glycosidase inhibition activity of these compounds against some commercially available enzymes was examined, and the analogues were found to be very selective glycosidase inhibitors at concentrations in the range of 21–44 μM.

  两种基于多羟基哌啶的 2-C-羟甲基支链的 L-1-脱氧异菌野尻霉素 (L-allo-DNJ) 类似物由现成的 1,2:5,6-二-O-异亚丙基-α-呋喃糖通过烯-炔复分解是关键步骤。检查了这些化合物对一些市售酶的糖苷酶抑制活性，发现类似物在 21–44 μM 的浓度范围内是非常有选择性的糖苷酶抑制剂。
• 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.