(3R,5S)-2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-3-(tert-butyldiphenylsilyloxymethyl)-5-cyanoisoxazolidine | 873920-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,5S)-2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-3-(tert-butyldiphenylsilyloxymethyl)-5-cyanoisoxazolidine
• 英文别名: (3R,5S)-2-[(3aR,4R,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-[[tert-butyl(diphenyl)silyl]oxymethyl]-1,2-oxazolidine-5-carbonitrile
• CAS: 873920-57-1
• 化学式: C₄₅H₅₆N₂O₆Si₂
• 分子量: 777.12
• InChiKey: HGKZZFCURVSHPF-KIONMSCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  55
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  82.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R,5S)-2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-3-(tert-butyldiphenylsilyloxymethyl)-5-cyanoisoxazolidine 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (3R,5S)-3-(tert-butyldiphenylsiloxymethyl)-5-cyanoisoxazolidine
  参考文献：
  名称：

  An efficient approach to enantiomeric isoxazolidinyl analogues of tiazofurin based on nitrone cycloadditions

  摘要：

  An efficient synthetic route to isoxazolidinyl analogues of tiazofurin has been developed. The strategy involves, as a key step, a 1,3-dipolar cycloaddition between acrylonitrile and chiral nonracemic nitrones. An opposite diastereofacial induction was observed when the chiral group was placed at either the carbon atom or the nitrogen one of the nitrone function. The 2-cyano isoxazolidines obtained were further converted into the enantiomeric target compounds by constructing the thiazole ring via condensation with L-cysteine. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.11.004
• 作为产物：
  描述：

  (tert-butyldiphenylsilanyloxy)acetaldehyde 、 丙烯腈 、 5-(tert-butyldiphenylsilyl)-1-deoxy-1-hydroxyamino-2,3-O-isopropylidene-β-D-ribo-1,4-pentofuranose 反应 12.0h， 生成 (3R,5S)-2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-3-(tert-butyldiphenylsilyloxymethyl)-5-cyanoisoxazolidine 、 (3S,5S)-2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-3-(tert-butyldiphenylsilyloxymethyl)-5-cyanoisoxazolidine 、 (3S,5R)-2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-3-(tert-butyldiphenylsilyloxymethyl)-5-cyanoisoxazolidine
  参考文献：
  名称：

  An efficient approach to enantiomeric isoxazolidinyl analogues of tiazofurin based on nitrone cycloadditions

  摘要：

  An efficient synthetic route to isoxazolidinyl analogues of tiazofurin has been developed. The strategy involves, as a key step, a 1,3-dipolar cycloaddition between acrylonitrile and chiral nonracemic nitrones. An opposite diastereofacial induction was observed when the chiral group was placed at either the carbon atom or the nitrogen one of the nitrone function. The 2-cyano isoxazolidines obtained were further converted into the enantiomeric target compounds by constructing the thiazole ring via condensation with L-cysteine. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.11.004

文献信息

• An efficient approach to enantiomeric isoxazolidinyl analogues of tiazofurin based on nitrone cycloadditions
  作者：Pedro Merino、Tomás Tejero、Francisco J. Unzurrunzaga、Santiago Franco、Ugo Chiacchio、Maria G. Saita、Daniela Iannazzo、Anna Piperno、Giovanni Romeo

  DOI：10.1016/j.tetasy.2005.11.004

  日期：2005.11

  An efficient synthetic route to isoxazolidinyl analogues of tiazofurin has been developed. The strategy involves, as a key step, a 1,3-dipolar cycloaddition between acrylonitrile and chiral nonracemic nitrones. An opposite diastereofacial induction was observed when the chiral group was placed at either the carbon atom or the nitrogen one of the nitrone function. The 2-cyano isoxazolidines obtained were further converted into the enantiomeric target compounds by constructing the thiazole ring via condensation with L-cysteine. (c) 2005 Elsevier Ltd. All rights reserved.