(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(tert-butyl-diphenyl-silanyloxy)-dihydro-furan-2-one | 176246-90-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(tert-butyl-diphenyl-silanyloxy)-dihydro-furan-2-one
• CAS: 176246-90-5
• 化学式: C₂₇H₄₀O₄Si₂
• 分子量: 484.783
• InChiKey: LSZWKKPYVSVVBY-BJKOFHAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(tert-butyl-diphenyl-silanyloxy)-dihydro-furan-2-one 在 吡啶 、 4-二甲氨基吡啶 、 三甲基溴硅烷 、 氢氟酸 、 sodium hydride 、 二异丁基氢化铝 、 溶剂黄146 作用下， 以 二氯甲烷 、 环己烷 、 甲苯 为溶剂， 反应 105.0h， 生成
  参考文献：
  名称：

  C-Glycosylphosphonyl Analogs of 5-Phosphorylribose 1-α-Diphosphate

  摘要：

  D-ribo-2,5-anhydro-1,3-dideoxy-1-(((dihydroxyphosphinyl)oxy) hydroxyphosphininyl)-6-phorylhexitol, compound 4, along with 25% of its D-arabino epimer, was synthesized in 10 steps from 2-deoxyribonolactone. Compound 4 represents the 2-deoxy analog of the central metabolite 5-phosphorylribose 1-alpha-diphosphate (PRPP). The analog is a competitive inhibitor of yeast orotate phosphoribosyltransferase (PRTase) with K-i/K-m(PRPP) = 24 and is thus comparable to other C-glycosylphosphonyl PRPP analogs reported previously (R. W. McClard, and J. F. Witte (1990) Bioorg. Chem. 18, 165-178). The analog is an even better inhibitor of both human hypoxanthine-guanine PRTase and glutamine:amido PRTase from Escherichia coli with K-i/K-m(PRPP) values of 16 and 3, respectively. These results support the argument that the cis-diol grouping of nucleotides (or PRPP) plays a very minor role in binding of these substrates to PRTases. (C) 1996 Academic Press, Inc.

  DOI：

  10.1006/bioo.1996.0004
• 作为产物：
  描述：

  D-(+)-核糖酸-gamma-内酯 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 32.0h， 生成 (4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(tert-butyl-diphenyl-silanyloxy)-dihydro-furan-2-one
  参考文献：
  名称：

  C-Glycosylphosphonyl Analogs of 5-Phosphorylribose 1-α-Diphosphate

  摘要：

  D-ribo-2,5-anhydro-1,3-dideoxy-1-(((dihydroxyphosphinyl)oxy) hydroxyphosphininyl)-6-phorylhexitol, compound 4, along with 25% of its D-arabino epimer, was synthesized in 10 steps from 2-deoxyribonolactone. Compound 4 represents the 2-deoxy analog of the central metabolite 5-phosphorylribose 1-alpha-diphosphate (PRPP). The analog is a competitive inhibitor of yeast orotate phosphoribosyltransferase (PRTase) with K-i/K-m(PRPP) = 24 and is thus comparable to other C-glycosylphosphonyl PRPP analogs reported previously (R. W. McClard, and J. F. Witte (1990) Bioorg. Chem. 18, 165-178). The analog is an even better inhibitor of both human hypoxanthine-guanine PRTase and glutamine:amido PRTase from Escherichia coli with K-i/K-m(PRPP) values of 16 and 3, respectively. These results support the argument that the cis-diol grouping of nucleotides (or PRPP) plays a very minor role in binding of these substrates to PRTases. (C) 1996 Academic Press, Inc.

  DOI：

  10.1006/bioo.1996.0004