1',2'-bis-O-(β-D-glucopyranosyl)-L-biopterin | 204642-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 1',2'-bis-O-(β-D-glucopyranosyl)-L-biopterin
• CAS: 204642-02-4
• 化学式: C₂₁H₃₁N₅O₁₃
• 分子量: 561.503
• InChiKey: KZKADCZROBBBSI-OLNVWXQGSA-N

反应信息

• 作为反应物：
  描述：

  1',2'-bis-O-(β-D-glucopyranosyl)-L-biopterin 、 乙酸酐 以 吡啶 为溶剂， 反应 12.0h， 以91%的产率得到N²-acetyl-1'-2'-bis-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-biopterin
  参考文献：
  名称：

  An Efficient Synthesis of 2’-O-(b-D-Glucopyranosyl)- and 2’-O-(2-Acetamido-2-deoxy-b-D-glucopyranosyl)-L-biopterins

  摘要：

  N-2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1',2'-di-O-trimethylsilyl-L-biopterin (6) was prepared from L-biopterin in 5 steps. Glycosylation of 6 with 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl trichloroacetimidate (9) and 1,3,4,6-tetra-O-acetyl-2-phtalimido-beta-D-glucopyranose (10) respectively afforded the corresponding 2'-O-(beta-D-glucopyranosyl) derivatives (12b, 12c) as major products. Removal of protecting groups of 12c provided naturally occurring limipterin (2).

  DOI：

  10.3987/com-05-s(t)28
• 作为产物：
  描述：

  N²-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1',2'-bis-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-biopterin 在 氨 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以92%的产率得到1',2'-bis-O-(β-D-glucopyranosyl)-L-biopterin
  参考文献：
  名称：

  An Efficient Synthesis of 2’-O-(b-D-Glucopyranosyl)- and 2’-O-(2-Acetamido-2-deoxy-b-D-glucopyranosyl)-L-biopterins

  摘要：

  N-2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1',2'-di-O-trimethylsilyl-L-biopterin (6) was prepared from L-biopterin in 5 steps. Glycosylation of 6 with 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl trichloroacetimidate (9) and 1,3,4,6-tetra-O-acetyl-2-phtalimido-beta-D-glucopyranose (10) respectively afforded the corresponding 2'-O-(beta-D-glucopyranosyl) derivatives (12b, 12c) as major products. Removal of protecting groups of 12c provided naturally occurring limipterin (2).

  DOI：

  10.3987/com-05-s(t)28