3-O-benzyl-2-deoxy-4,5-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-psicopyranose | 876374-12-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3-O-benzyl-2-deoxy-4,5-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-psicopyranose
• CAS: 876374-12-8
• 化学式: C₁₉H₂₉NO₉S₂
• 分子量: 479.573
• InChiKey: CNVJTBHAIYDXLH-YWTNHNAXSA-N

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-2-deoxy-4,5-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-psicopyranose 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以54%的产率得到(7R,8R,9R)-2-aza-9-benzyloxy-7,8-(dimethylmethylenedioxy)-2-N-mesyl-5-oxaspiro[3.5]nonane
  参考文献：
  名称：

  Expeditious synthesis of sulfoazetidine spiro-C-glycosides from ketose acetals

  摘要：

  Pyranoid and furanoid spiro-N-mesyl azetidines, a new type of water-soluble spiro-C-nucleoside, have been prepared from easily available sugar spiroacetals (or glycosyl cyanides). The synthetic pathway involves opening of the acetalic ring with trimethylsilylcyanide, reduction, formation of an N,O-dimesylate, cyclization with sodium hydride in anhydrous DMF, and O-deprotection. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.038
• 作为产物：
  描述：

  3-O-benzyl-2-cyano-2-deoxy-4,5-O-isopropylidene-β-D-psicopyranose 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 24.0h， 生成 3-O-benzyl-2-deoxy-4,5-O-isopropylidene-1-O-mesyl-2-mesylaminomethyl-β-D-psicopyranose
  参考文献：
  名称：

  Expeditious synthesis of sulfoazetidine spiro-C-glycosides from ketose acetals

  摘要：

  Pyranoid and furanoid spiro-N-mesyl azetidines, a new type of water-soluble spiro-C-nucleoside, have been prepared from easily available sugar spiroacetals (or glycosyl cyanides). The synthetic pathway involves opening of the acetalic ring with trimethylsilylcyanide, reduction, formation of an N,O-dimesylate, cyclization with sodium hydride in anhydrous DMF, and O-deprotection. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.038