(3Z)-5-bromo-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-β-L-lyxo-hex-3-enofuranose | 188249-27-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3Z)-5-bromo-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-β-L-lyxo-hex-3-enofuranose
• CAS: 188249-27-6
• 化学式: C₂₉H₃₇BrO₆Si
• 分子量: 589.599
• InChiKey: AHBSXRGISNPEBI-UHFZTYSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3Z)-5-bromo-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-β-L-lyxo-hex-3-enofuranose 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以40%的产率得到5-bromo-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethyl-1,2-O-isopropylidene-β-L-talofuranose
  参考文献：
  名称：

  Synthesis and Reactions of 3-C-Branched-Chain Analogues of 3,6-Anhydrodeoxynojirimycin

  摘要：

  The syntheses of 3,6-anhydro-1-deoxy-3-C-ethoxycarbonylmethyl- (4) and 3-C-(2-hydroxyethyl)nojirimycin (5) from 5-azido-6-O-tert-butyldiphenylsiyl-5-deoxy-1,2-O-isopropylidene-alpha-D-glucofuranose (8) are described. The key intermediate is 5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-alpha-D-ribo-hex-3-enofuranose (11) which was obtained by condensation of 5-azido-6-O-tertbutyldiphenylsilyl-5-deoxy- 1,2-O-isopropylidene-alpha-D-ribo-hexos-3-ulofuranose (10) with (ethoxycarbonylmethylene)triphenylphosphorane. Conventional benzoylation of 4 resulted in the formation of the lactones 13a and 13b. The 3-C-(2-hydroxyethyl) analogue (5) was synthesized by lithium aluminum hydride reduction of 3,6-anhydroxy-5-azido-5-deoxy-3-C-ethoxycarbonylmethyl- 1,2-O-isopropylidene-alpha-D-glucofuranose (12), followed by deacetalation, and hydrogenation.

  DOI：

  10.1080/07328309708006509
• 作为产物：
  描述：

  1,2-O-isopropylidene-6-tert-butyldiphenylsilyl-α-D-glucofuranose 在 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 重铬酸吡啶 、 3 A molecular sieve 、 sodium methylate 、 溶剂黄146 、 barium carbonate 、 zinc(II) chloride 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 23.17h， 生成 (3Z)-5-bromo-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-β-L-lyxo-hex-3-enofuranose
  参考文献：
  名称：

  Synthesis and Reactions of 3-C-Branched-Chain Analogues of 3,6-Anhydrodeoxynojirimycin

  摘要：

  The syntheses of 3,6-anhydro-1-deoxy-3-C-ethoxycarbonylmethyl- (4) and 3-C-(2-hydroxyethyl)nojirimycin (5) from 5-azido-6-O-tert-butyldiphenylsiyl-5-deoxy-1,2-O-isopropylidene-alpha-D-glucofuranose (8) are described. The key intermediate is 5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-alpha-D-ribo-hex-3-enofuranose (11) which was obtained by condensation of 5-azido-6-O-tertbutyldiphenylsilyl-5-deoxy- 1,2-O-isopropylidene-alpha-D-ribo-hexos-3-ulofuranose (10) with (ethoxycarbonylmethylene)triphenylphosphorane. Conventional benzoylation of 4 resulted in the formation of the lactones 13a and 13b. The 3-C-(2-hydroxyethyl) analogue (5) was synthesized by lithium aluminum hydride reduction of 3,6-anhydroxy-5-azido-5-deoxy-3-C-ethoxycarbonylmethyl- 1,2-O-isopropylidene-alpha-D-glucofuranose (12), followed by deacetalation, and hydrogenation.

  DOI：

  10.1080/07328309708006509