5-O-tert-butyldiphenylsilyl-3-deoxy-3-isothiocyanato-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose | 1379002-59-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-tert-butyldiphenylsilyl-3-deoxy-3-isothiocyanato-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose
• CAS: 1379002-59-1
• 化学式: C₂₇H₃₃NO₆SSi
• 分子量: 527.714
• InChiKey: IIDMRBFNKSDZLP-IQXSCUCBSA-N

物化性质

• 沸点：
  556.3±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  75.58
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-O-tert-butyldiphenylsilyl-3-deoxy-3-isothiocyanato-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 49.5h， 生成 (5R,6S,8S,9S)-3-cyclohexyl-8,9-(dimethylmethylenedioxy)-6-hydroxymethyl-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one
  参考文献：
  名称：

  Synthesis of conformationally-constrained thio(seleno)hydantoins and α-triazolyl lactones from d-arabinose as potential glycosidase inhibitors

  摘要：

  We have explored the rich structural diversity provided by an a-azido ester derived from D-arabinose as the source of sugar templates with reduced conformational flexibility. Using transient alpha-thioureido(selenoureido) esters we have prepared spiranic thio(seleno)hydantoins at the C-3 position of the sugar moiety. In this context, the first example of a stable spiranic alpha-lactam (or aziridinone) was isolated as a by-product in the hydrogenolysis of the starting alpha-azido ester. Furthermore, using copper(I)-catalyzed azido-alkyne cycloaddition (click chemistry), we have accessed bicyclic cis-fused alpha-triazolyl lactones fixed in the furanose form. Spiranic thiohydantoins turned out to be moderate, though selective, inhibitors of glycosidases, whereas their selenium isosters behaved as good free radical scavengers. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.087
• 作为产物：
  描述：

  3-C-azido-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose 在 palladium 10% on activated carbon 、 氢气 、 calcium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 0.83h， 生成 5-O-tert-butyldiphenylsilyl-3-deoxy-3-isothiocyanato-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose
  参考文献：
  名称：

  Synthesis of conformationally-constrained thio(seleno)hydantoins and α-triazolyl lactones from d-arabinose as potential glycosidase inhibitors

  摘要：

  We have explored the rich structural diversity provided by an a-azido ester derived from D-arabinose as the source of sugar templates with reduced conformational flexibility. Using transient alpha-thioureido(selenoureido) esters we have prepared spiranic thio(seleno)hydantoins at the C-3 position of the sugar moiety. In this context, the first example of a stable spiranic alpha-lactam (or aziridinone) was isolated as a by-product in the hydrogenolysis of the starting alpha-azido ester. Furthermore, using copper(I)-catalyzed azido-alkyne cycloaddition (click chemistry), we have accessed bicyclic cis-fused alpha-triazolyl lactones fixed in the furanose form. Spiranic thiohydantoins turned out to be moderate, though selective, inhibitors of glycosidases, whereas their selenium isosters behaved as good free radical scavengers. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.087