(2S,3R,4R,5R)-2,3-bis(benzyloxy)-4-hydroxycyclohex-1-ene-ethane-5,6-diol-O-isopropylidene-1-(triisopropylsilyloxymethyl) | 1597438-25-9

• 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)-4-hydroxycyclohex-1-ene-ethane-5,6-diol-O-isopropylidene-1-(triisopropylsilyloxymethyl)
• 英文别名: (1R,5S,6R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-5,6-bis(phenylmethoxy)-4-[tri(propan-2-yl)silyloxymethyl]cyclohex-3-en-1-ol
• CAS: 1597438-25-9
• 化学式: C₃₅H₅₂O₆Si
• 分子量: 596.88
• InChiKey: BCGIQYWEEUKPPK-NAEZBXHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.56
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R)-2,3-bis(benzyloxy)-4-hydroxycyclohex-1-ene-ethane-5,6-diol-O-isopropylidene-1-(triisopropylsilyloxymethyl) 在 tetra-n-butylammoniumfluoride trihydrate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以84%的产率得到(2S,3R,4R,5R)-2,3-bis(benzyloxy)-4-hydroxycyclohex-1-ene-1-hydroxymethyl-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
• 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) 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以1.1 g的产率得到(2S,3R,4S,5R)-2,3-bis(benzyloxy)-4-hydroxycyclohex-1-ene-ethane-5,6-diol-O-isopropylidene-1-(triisopropylsilyloxymethyl)
  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