6-O-tert-butyldiphenylsilyl-5-deoxy-5-iodo-1,2-O-isopropylidene-β-L-idofuranose | 188249-09-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-tert-butyldiphenylsilyl-5-deoxy-5-iodo-1,2-O-isopropylidene-β-L-idofuranose
• CAS: 188249-09-4
• 化学式: C₂₅H₃₃IO₅Si
• 分子量: 568.524
• InChiKey: UODYJTGTLKWZTA-LHGONGGSSA-N

反应信息

• 作为反应物：
  描述：

  6-O-tert-butyldiphenylsilyl-5-deoxy-5-iodo-1,2-O-isopropylidene-β-L-idofuranose 在 sodium azide 、 重铬酸吡啶 、 3 A molecular sieve 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 9.5h， 以57.8%的产率得到5-azido-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexos-3-ulofuranose
  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：

  3-O-benzoyl-6-O-tert-butyldiphenylsilyl-5-deoxy-5-iodo-1,2-O-isopropylidene-β-L-idofuranose 在 甲醇 、 sodium methylate 作用下， 反应 4.0h， 以78.3%的产率得到6-O-tert-butyldiphenylsilyl-5-deoxy-5-iodo-1,2-O-isopropylidene-β-L-idofuranose
  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