tert-butyl N-[5-[(3aR,4S,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1,3-thiazol-2-yl]-N-methylcarbamate | 543729-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl N-[5-[(3aR,4S,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1,3-thiazol-2-yl]-N-methylcarbamate
• CAS: 543729-95-9
• 化学式: C₃₃H₄₄N₂O₆SSi
• 分子量: 624.874
• InChiKey: QWMQTFGUNJVLPW-YULOIDQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[5-[(3aR,4S,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1,3-thiazol-2-yl]-N-methylcarbamate 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 以93%的产率得到(2R,3S,4R,5S)-2-Hydroxymethyl-5-(2-methylamino-thiazol-5-yl)-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  A short and highly stereoselective synthesis of α-(2-aminothiazolyl)-C-nucleosides

  摘要：

  A short route to novel alpha-(2-aminothiazolyl)-C-nucleosides has been developed. The key step was the high diastereoselective reduction of the hemiacetal intermediates using L-Selectride, which afforded the corresponding R-diols in quantitative yields. These diols were converted, after C4-C1 ring closure and protecting groups cleavage, to their corresponding free alpha-C-nucleosides. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00159-x
• 作为产物：
  描述：

  噻唑-2-氨基甲酸叔丁酯 在 L-Selectride 、 sodium hydride 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 tert-butyl N-[5-[(3aR,4S,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1,3-thiazol-2-yl]-N-methylcarbamate
  参考文献：
  名称：

  A short and highly stereoselective synthesis of α-(2-aminothiazolyl)-C-nucleosides

  摘要：

  A short route to novel alpha-(2-aminothiazolyl)-C-nucleosides has been developed. The key step was the high diastereoselective reduction of the hemiacetal intermediates using L-Selectride, which afforded the corresponding R-diols in quantitative yields. These diols were converted, after C4-C1 ring closure and protecting groups cleavage, to their corresponding free alpha-C-nucleosides. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00159-x

文献信息

• A short and highly stereoselective synthesis of α-(2-aminothiazolyl)-C-nucleosides
  作者：Jean-Michel Navarre、Dominique Guianvarc'h、Audrey Farese-Di Giorgio、Roger Condom、Rachid Benhida

  DOI：10.1016/s0040-4039(03)00159-x

  日期：2003.3

  A short route to novel alpha-(2-aminothiazolyl)-C-nucleosides has been developed. The key step was the high diastereoselective reduction of the hemiacetal intermediates using L-Selectride, which afforded the corresponding R-diols in quantitative yields. These diols were converted, after C4-C1 ring closure and protecting groups cleavage, to their corresponding free alpha-C-nucleosides. (C) 2003 Elsevier Science Ltd. All rights reserved.