(2S,3R,4R,5R)-2,3-bis(benzyloxy)-1-(dimethoxyphosphoryl)methyl-4-hydroxy cyclohex-1-ene-ethane-5,6-diol-O-isopropylidene | 1597438-27-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5R)-2,3-bis(benzyloxy)-1-(dimethoxyphosphoryl)methyl-4-hydroxy cyclohex-1-ene-ethane-5,6-diol-O-isopropylidene
• CAS: 1597438-27-1
• 化学式: C₂₈H₃₇O₈P
• 分子量: 532.571
• InChiKey: FWBXKRQVFPEBDW-IYOUEGCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R)-2,3-bis(benzyloxy)-1-(dimethoxyphosphoryl)methyl-4-hydroxy cyclohex-1-ene-ethane-5,6-diol-O-isopropylidene 在 三甲基溴硅烷 、 氢气 、 palladium(II) hydroxide 作用下， 以 二氯甲烷 、 甲醇 、 乙酸乙酯 为溶剂， 反应 2.83h， 以100%的产率得到C-[(2S,3R,4R,5R)-cyclohex-1-ene-5,6-ethane-2,3,4,5,6-pentaol]methylphosphonic acid
  参考文献：
  名称：

  Synthesis of a Novel UDP-carbasugar as UDP-galactopyranose Mutase Inhibitor

  摘要：

  The multistep synthesis of a novel UDP-C-cyclohexene, designed as a high energy intermediate analogue of the UDP-galactopyranose mutase (UGM) catalyzed isomerization reaction, is reported. The synthesis of the central carbasugar involved the preparation of a galactitol derivative bearing two olefins necessary for the construction of the cyclohexene ring by a ring-closing metathesis as a key step. Further successive phosphonylation, deprotection, and UMP coupling provided the target molecule. The final molecule was assayed against UGM and compared with UDP-C-Galf, the C-glycosidic UGM substrate analogue.

  DOI：

  10.1021/ol500848q
• 作为产物：
  描述：

  2,3-di-O-benzyl-1,4’’,4’”-trideoxy-1-C-methylene-5,6-O-isopropylidene-1’-tri-Oisopropylsilyl-4-C-(prop-4’-enyl)-D-galacto-heptitol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 tetra-n-butylammoniumfluoride trihydrate 、 zinc dibromide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 11.0h， 生成 (2S,3R,4R,5R)-2,3-bis(benzyloxy)-1-(dimethoxyphosphoryl)methyl-4-hydroxy cyclohex-1-ene-ethane-5,6-diol-O-isopropylidene
  参考文献：
  名称：

  Synthesis of a Novel UDP-carbasugar as UDP-galactopyranose Mutase Inhibitor

  摘要：

  The multistep synthesis of a novel UDP-C-cyclohexene, designed as a high energy intermediate analogue of the UDP-galactopyranose mutase (UGM) catalyzed isomerization reaction, is reported. The synthesis of the central carbasugar involved the preparation of a galactitol derivative bearing two olefins necessary for the construction of the cyclohexene ring by a ring-closing metathesis as a key step. Further successive phosphonylation, deprotection, and UMP coupling provided the target molecule. The final molecule was assayed against UGM and compared with UDP-C-Galf, the C-glycosidic UGM substrate analogue.

  DOI：

  10.1021/ol500848q