Acetic acid (2R,3S,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-6-(bis-benzyloxy-phosphoryloxy)-5-methoxy-tetrahydro-pyran-4-yl ester | 187102-58-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-6-(bis-benzyloxy-phosphoryloxy)-5-methoxy-tetrahydro-pyran-4-yl ester
• CAS: 187102-58-5
• 化学式: C₂₇H₃₃O₁₂P
• 分子量: 580.526
• InChiKey: BPDLKYKBKPGXLQ-LXSUACKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  40.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  142.12
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-6-(bis-benzyloxy-phosphoryloxy)-5-methoxy-tetrahydro-pyran-4-yl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Novel aspects of interaction between UDP-Gal and GlcNAc β-1,4-Galactosyltransferase: Transferability and remarkable inhibitory activity of UDP-(mono-O-methylated Gal), UDP-Fuc and UDP-Man

  摘要：

  Four mono-O-methylated and one mono-O-acetylated UDP-D-Gal analogues and UDP-L-Fuc were synthesized. 2-O-Methyl-D-galactose residue was enzymatically transferred to give 2'-O-methyIlactosaminide in high yield. UDP-Fuc and UDP-Man showed potent inhibitory activities against beta-1,4-galactosyltransferase. Structural requirement and steric allowance for the ground and transition states of the enzyme reaction were discussed. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00176-9
• 作为产物：
  描述：

  二苄基磷酰基氯 、 3,4,6-tri-O-acetyl-2-O-methyl-D-galactopyranose 在 正丁基锂 作用下， 生成 Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-6-(bis-benzyloxy-phosphoryloxy)-5-methoxy-tetrahydro-pyran-4-yl ester 、 Acetic acid (2R,3S,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-6-(bis-benzyloxy-phosphoryloxy)-5-methoxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Novel aspects of interaction between UDP-Gal and GlcNAc β-1,4-Galactosyltransferase: Transferability and remarkable inhibitory activity of UDP-(mono-O-methylated Gal), UDP-Fuc and UDP-Man

  摘要：

  Four mono-O-methylated and one mono-O-acetylated UDP-D-Gal analogues and UDP-L-Fuc were synthesized. 2-O-Methyl-D-galactose residue was enzymatically transferred to give 2'-O-methyIlactosaminide in high yield. UDP-Fuc and UDP-Man showed potent inhibitory activities against beta-1,4-galactosyltransferase. Structural requirement and steric allowance for the ground and transition states of the enzyme reaction were discussed. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00176-9