dibenzyl 2,3,6-tri-O-acetyl-4-deoxy-α-D-mannose-1-phosphate | 139493-75-7

• 英文名称: dibenzyl 2,3,6-tri-O-acetyl-4-deoxy-α-D-mannose-1-phosphate
• 英文别名: Dibenzyl 2,3,6-tri-O-acetyl-4-deoxy-α-D-lyxo hexopyranosyl phosphate；[(2S,4S,5S,6R)-4,5-diacetyloxy-6-bis(phenylmethoxy)phosphoryloxyoxan-2-yl]methyl acetate
• CAS: 139493-75-7
• 化学式: C₂₆H₃₁O₁₁P
• 分子量: 550.499
• InChiKey: MMZDLVZSJGDHNL-ASDGIDEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  dibenzyl 2,3,6-tri-O-acetyl-4-deoxy-α-D-mannose-1-phosphate 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 Disodium (4-deoxy-α-D-lyxo-hexopyranosyl phosphate)
  参考文献：
  名称：

  Niggemann, Jutta; Thiem, Joachim, Liebigs Annalen der Chemie, 1992, # 5, p. 535 - 538

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,6-Tetra-O-acetyl-4-deoxy-α-D-lyxo-hexopyranose 在 苄胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 反应 24.75h， 生成 dibenzyl 2,3,6-tri-O-acetyl-4-deoxy-α-D-mannose-1-phosphate
  参考文献：
  名称：

  The preparation of deoxy derivatives of mannose-1-phosphate and their substrate specificity towards recombinant GDP-mannose pyrophosphorylase from Salmonella enterica, group B

  摘要：

  2-Deoxy-alpha-D-glucose-1-phosphate, 3-deoxy-alpha-D-arabino-hexose-1-phosphate, 4-deoxy-alpha-D-lyxo-hexose-1-phosphate, and alpha-D-lyxose-1-phosphate were synthesised chemically, and evaluated as substrates for a recombinant GDP-mannose pyrophosphorylase (Salmonella enterica, group B, cloned in Escherichia coli). The deoxy derivatives were all substrates for the enzyme, with slightly reduced V-max values but significantly higher K-m values than those recorded for the native substrate, mannose-1-phosphate. The pyrophosphorylase was used for the synthesis of GDP-mannose analogues GDP-2-deoxy-glucose and GDP-lyxose on a milligram scale. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00556-x