(E)-N-(tert-butoxycarbonyl)-2,3,4,7-tetradeoxy-4,7-imino-5,6-O-isopropylidene-L-ribo-hept-2-enitol | 674810-63-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (E)-N-(tert-butoxycarbonyl)-2,3,4,7-tetradeoxy-4,7-imino-5,6-O-isopropylidene-L-ribo-hept-2-enitol
• 英文别名: tert-butyl (3aR,4R,6aS)-4-[(E)-3-hydroxyprop-1-enyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 674810-63-0
• 化学式: C₁₅H₂₅NO₅
• 分子量: 299.367
• InChiKey: HNLOHEMFJSXJIP-VQSFLMFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-N-(tert-butoxycarbonyl)-2,3,4,7-tetradeoxy-4,7-imino-5,6-O-isopropylidene-L-ribo-hept-2-enitol 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 甲基磺酰胺 、 sodium methylate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 80.5h， 生成 (3aR,4R,6aS)-4-[(1R,2R)-1,2-Dihydroxy-3-(toluene-4-sulfonyloxy)-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of novel tetrahydroxypyrrolizidines

  摘要：

  N-Benzyloxycarbonyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-L-ribose 12a has been converted into (1R,2S,6R, 7S,7aS)-5 and (1R, 2S, 6S, 7R, 7aR)-1,2,6,7-tetrahydroxypyrrolidin-5-ones 6 and (1R,2S,6S,7S,7aS)-7 and (1R,2S,6R,7R,7aS)-1,2,6,7-tetrahydroxypyrrolizidines 8 following stereoselective paths. These new compounds have been assayed for their inhibitory activities towards 25 glycosidases. Pyrrolizidines 7 and 8 are moderate but selective inhibitors of amyloglucosidase from Rhizopus mold (7: IC50 = 130 muM, K-i = 120 muM; 8: IC50 = 200 muM, K-i = 180 muM, mixed type of inhibition). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.022
• 作为产物：
  描述：

  2,5-{[(tert-butoxy)carbonyl]imino}-2,5-dideoxy-3,4-O-isopropylidene-L-ribose 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 生成 (E)-N-(tert-butoxycarbonyl)-2,3,4,7-tetradeoxy-4,7-imino-5,6-O-isopropylidene-L-ribo-hept-2-enitol
  参考文献：
  名称：

  Stereoselective synthesis of novel tetrahydroxypyrrolizidines

  摘要：

  N-Benzyloxycarbonyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-L-ribose 12a has been converted into (1R,2S,6R, 7S,7aS)-5 and (1R, 2S, 6S, 7R, 7aR)-1,2,6,7-tetrahydroxypyrrolidin-5-ones 6 and (1R,2S,6S,7S,7aS)-7 and (1R,2S,6R,7R,7aS)-1,2,6,7-tetrahydroxypyrrolizidines 8 following stereoselective paths. These new compounds have been assayed for their inhibitory activities towards 25 glycosidases. Pyrrolizidines 7 and 8 are moderate but selective inhibitors of amyloglucosidase from Rhizopus mold (7: IC50 = 130 muM, K-i = 120 muM; 8: IC50 = 200 muM, K-i = 180 muM, mixed type of inhibition). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.022

文献信息

• Stereoselective synthesis of novel tetrahydroxypyrrolizidines
  作者：Ana T. Carmona、José Fuentes、Pierre Vogel、Inmaculada Robina

  DOI：10.1016/j.tetasy.2003.11.022

  日期：2004.1

  N-Benzyloxycarbonyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-L-ribose 12a has been converted into (1R,2S,6R, 7S,7aS)-5 and (1R, 2S, 6S, 7R, 7aR)-1,2,6,7-tetrahydroxypyrrolidin-5-ones 6 and (1R,2S,6S,7S,7aS)-7 and (1R,2S,6R,7R,7aS)-1,2,6,7-tetrahydroxypyrrolizidines 8 following stereoselective paths. These new compounds have been assayed for their inhibitory activities towards 25 glycosidases. Pyrrolizidines 7 and 8 are moderate but selective inhibitors of amyloglucosidase from Rhizopus mold (7: IC50 = 130 muM, K-i = 120 muM; 8: IC50 = 200 muM, K-i = 180 muM, mixed type of inhibition). (C) 2003 Elsevier Ltd. All rights reserved.