(3a'S,4'S,5'S)-4',5'-bis(tert-butyldimethylsilyloxy)hexahydrospiro(cyclopropane-1,2'-pyrrolo[1,2-b]isoxazole) | 180139-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (3a'S,4'S,5'S)-4',5'-bis(tert-butyldimethylsilyloxy)hexahydrospiro(cyclopropane-1,2'-pyrrolo[1,2-b]isoxazole)
• CAS: 180139-82-6
• 化学式: C₂₀H₄₁NO₃Si₂
• 分子量: 399.721
• InChiKey: YUHUKKGCFPJRHB-ULQDDVLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  30.93
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3a'S,4'S,5'S)-4',5'-bis(tert-butyldimethylsilyloxy)hexahydrospiro(cyclopropane-1,2'-pyrrolo[1,2-b]isoxazole) 在 lithium tri-sec-butyl(hydrido)borate 作用下， 生成 (1S,2S,7S,8aS)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-octahydro-indolizin-7-ol
  参考文献：
  名称：

  (1S,2S,7R,8aS)- and (1S,2S,7S,8aS)-trihydroxyoctahydroindolizine: Two new glycosidase inhibitors by nitrone cycloaddition strategy

  摘要：

  The two new epimeric (1S,2S,7R,8aS)- and (1S,2S,7S,8aS)-1,2,7-trihydroxyoctahydroindolizines 4 and 5 have been synthesized via methylenecyclopropane-nitrone cycloaddition-rearrangement methodology employing an enantiomerically pure L-tartaric acid derived nitrone 7b. Highly stereoselective reductions of the intermediate indolizidinone 10b and final deprotection furnished the two title indolizidinetriols 4 and 5, the inhibiting abilities of which toward 24 commercially available glycosidases were tested. Both 4 and 5 are good competitive inhibitors of amyloglucosidases with K-i values of ca. 6 and 75 mu M, respectively. Compared with (+)-lentiginosine 3, 4 and 5 are less powerful inhibitors but, in contrast to 3, the (7R)-hydroxy analogue 4 possesses a weak inhibiting activity toward alpha-L-fucosidase from bovine epididymis. A model to rationalize the structure-activity relationship of (+)-lentiginosine and the two new 7-hydroxylentiginosines toward glucoamylases is proposed on the basis of their structural comparison with known inhibitors and with the natural enzyme's substrate amylose. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00200-5
• 作为产物：
  描述：

  (3S,4s)-3,4-双[[(1,1-二甲基乙基)二甲基甲硅烷基]氧基]吡咯烷 在 selenium(IV) oxide 、 双氧水 作用下， 以 丙酮 、 苯 为溶剂， 反应 265.0h， 生成 (3a'S,4'S,5'S)-4',5'-bis(tert-butyldimethylsilyloxy)hexahydrospiro(cyclopropane-1,2'-pyrrolo[1,2-b]isoxazole)
  参考文献：
  名称：

  (1S,2S,7R,8aS)- and (1S,2S,7S,8aS)-trihydroxyoctahydroindolizine: Two new glycosidase inhibitors by nitrone cycloaddition strategy

  摘要：

  The two new epimeric (1S,2S,7R,8aS)- and (1S,2S,7S,8aS)-1,2,7-trihydroxyoctahydroindolizines 4 and 5 have been synthesized via methylenecyclopropane-nitrone cycloaddition-rearrangement methodology employing an enantiomerically pure L-tartaric acid derived nitrone 7b. Highly stereoselective reductions of the intermediate indolizidinone 10b and final deprotection furnished the two title indolizidinetriols 4 and 5, the inhibiting abilities of which toward 24 commercially available glycosidases were tested. Both 4 and 5 are good competitive inhibitors of amyloglucosidases with K-i values of ca. 6 and 75 mu M, respectively. Compared with (+)-lentiginosine 3, 4 and 5 are less powerful inhibitors but, in contrast to 3, the (7R)-hydroxy analogue 4 possesses a weak inhibiting activity toward alpha-L-fucosidase from bovine epididymis. A model to rationalize the structure-activity relationship of (+)-lentiginosine and the two new 7-hydroxylentiginosines toward glucoamylases is proposed on the basis of their structural comparison with known inhibitors and with the natural enzyme's substrate amylose. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00200-5

文献信息

• (1S,2S,7R,8aS)- and (1S,2S,7S,8aS)-trihydroxyoctahydroindolizine: Two new glycosidase inhibitors by nitrone cycloaddition strategy
  作者：Andrea Goti、Francesca Cardona、Alberto Brandi、Sylviane Picasso、Pierre Vogel

  DOI：10.1016/0957-4166(96)00200-5

  日期：1996.6

  The two new epimeric (1S,2S,7R,8aS)- and (1S,2S,7S,8aS)-1,2,7-trihydroxyoctahydroindolizines 4 and 5 have been synthesized via methylenecyclopropane-nitrone cycloaddition-rearrangement methodology employing an enantiomerically pure L-tartaric acid derived nitrone 7b. Highly stereoselective reductions of the intermediate indolizidinone 10b and final deprotection furnished the two title indolizidinetriols 4 and 5, the inhibiting abilities of which toward 24 commercially available glycosidases were tested. Both 4 and 5 are good competitive inhibitors of amyloglucosidases with K-i values of ca. 6 and 75 mu M, respectively. Compared with (+)-lentiginosine 3, 4 and 5 are less powerful inhibitors but, in contrast to 3, the (7R)-hydroxy analogue 4 possesses a weak inhibiting activity toward alpha-L-fucosidase from bovine epididymis. A model to rationalize the structure-activity relationship of (+)-lentiginosine and the two new 7-hydroxylentiginosines toward glucoamylases is proposed on the basis of their structural comparison with known inhibitors and with the natural enzyme's substrate amylose. Copyright (C) 1996 Elsevier Science Ltd