2,3-dideoxy-6-O-triphenylmethyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-β-D-glucopyranose | 742102-74-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2,3-dideoxy-6-O-triphenylmethyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-β-D-glucopyranose
• 英文别名: tert-butyl N-[[(2R,5S,6R)-5-hydroxy-6-(trityloxymethyl)oxan-2-yl]methyl]carbamate
• CAS: 742102-74-5
• 化学式: C₃₁H₃₇NO₅
• 分子量: 503.638
• InChiKey: YJDGAEPKTJIASX-OZNIXHKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-dideoxy-6-O-triphenylmethyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-β-D-glucopyranose 在 ruthenium trichloride 、 氢氧化钾 、 sodium hydroxide 、 dipotassium peroxodisulfate 、 四丁基硫酸氢铵 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 (1R,4S,5S)-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-tetrahydropyran-6-carboxylic acid
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Su- gar Amino Acid Based Inhibitors of Pro- tein Prenyl Transferases PFT and PGGT-1

  摘要：

  Eleven analogues of the C-terminal Ca(1)a(2)X Motif found in natural substrates of the prenyl transferases PFT and PGGT-1 were synthesized and evaluated for their inhibition potency and selectivity against PFT and PGGT-1. Replacement of the central dipeptide part a(1)a(2) by a benzylated sugar amino acid resulted in a good and highly selective PFT inhibitor (8, IC50 = 250 +/- 20 nM). The methyl ester of 8 (13) selectively inhibited protein farnesylation in cultured cells.

  DOI：

  10.1021/jm049927q
• 作为产物：
  描述：

  Acetic acid (2R,3S,6R)-2-acetoxymethyl-6-aminomethyl-tetrahydro-pyran-3-yl ester; hydrochloride 在 吡啶 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2,3-dideoxy-6-O-triphenylmethyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-β-D-glucopyranose
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Su- gar Amino Acid Based Inhibitors of Pro- tein Prenyl Transferases PFT and PGGT-1

  摘要：

  Eleven analogues of the C-terminal Ca(1)a(2)X Motif found in natural substrates of the prenyl transferases PFT and PGGT-1 were synthesized and evaluated for their inhibition potency and selectivity against PFT and PGGT-1. Replacement of the central dipeptide part a(1)a(2) by a benzylated sugar amino acid resulted in a good and highly selective PFT inhibitor (8, IC50 = 250 +/- 20 nM). The methyl ester of 8 (13) selectively inhibited protein farnesylation in cultured cells.

  DOI：

  10.1021/jm049927q

文献信息

• Design, Synthesis, and Evaluation of Su- gar Amino Acid Based Inhibitors of Pro- tein Prenyl Transferases PFT and PGGT-1
  作者：Farid El Oualid、Brigitte E. A. Burm、Ingrid M. Leroy、Louis H. Cohen、Jacques H. van Boom、Hans van den Elst、Herman S. Overkleeft、Gijs A. van der Marel、Mark Overhand

  DOI：10.1021/jm049927q

  日期：2004.7.1

  Eleven analogues of the C-terminal Ca(1)a(2)X Motif found in natural substrates of the prenyl transferases PFT and PGGT-1 were synthesized and evaluated for their inhibition potency and selectivity against PFT and PGGT-1. Replacement of the central dipeptide part a(1)a(2) by a benzylated sugar amino acid resulted in a good and highly selective PFT inhibitor (8, IC50 = 250 +/- 20 nM). The methyl ester of 8 (13) selectively inhibited protein farnesylation in cultured cells.