2,3-dideoxy-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-α-D-glucopyranose | 229473-27-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-dideoxy-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-α-D-glucopyranose
• CAS: 229473-27-2
• 化学式: C₁₂H₂₃NO₅
• 分子量: 261.318
• InChiKey: URKSLIOFSBTNBP-LPEHRKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  88.02
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,3-dideoxy-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-α-D-glucopyranose 在 二异丁基氢化铝 、 (+)-10-camphorsulfonic acid 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 2.5h， 生成 2,3-dideoxy-4-O-benzyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-α-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
• 作为产物：
  描述：

  Acetic acid (2R,3S,6S)-2-acetoxymethyl-6-(tert-butoxycarbonylamino-methyl)-tetrahydro-pyran-3-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以4.16 g的产率得到2,3-dideoxy-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-α-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