N²-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1',2'-di-O-trimethylsily-L-biopterin | 186752-55-6

• 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: N²-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1',2'-di-O-trimethylsily-L-biopterin
• 英文别名: N'-[6-[(1R,2S)-1,2-bis(trimethylsilyloxy)propyl]-3-[2-(4-nitrophenyl)ethyl]-4-oxopteridin-2-yl]-N,N-dimethylmethanimidamide
• CAS: 186752-55-6
• 化学式: C₂₆H₃₉N₇O₅Si₂
• 分子量: 585.811
• InChiKey: NPOUXQHQMGPGGY-WDZJVADNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N²-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1',2'-di-O-trimethylsily-L-biopterin 在 氨 、 四氯化锡 、 甲胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 84.0h， 生成 limipterin
  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：

  L-生物蝶呤 在 硫酸氢铵 、 TEA 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 79.0h， 生成 N²-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1',2'-di-O-trimethylsily-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

文献信息

• An Efficient Synthesis of 2’-O-(b-D-Glucopyranosyl)- and 2’-O-(2-Acetamido-2-deoxy-b-D-glucopyranosyl)-L-biopterins
  作者：Tadashi Hanaya、Kazuyuki Soranaka、Koichiro Harada、Hiroshi Yamaguchi、Ryo Suzuki、Yusumi Endo、Hiroshi Yamamoto、Wolfgang Pfleiderer

  DOI：10.3987/com-05-s(t)28

  日期：——

  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).