[(2S,4S,5S,6R)-4,5,6-tribenzoyloxyoxan-2-yl]methyl benzoate | 286843-90-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2S,4S,5S,6R)-4,5,6-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 286843-90-1
• 化学式: C₃₄H₂₈O₉
• 分子量: 580.591
• InChiKey: HFXCSBKFHIKCNA-GDDXUJBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  [(2S,4S,5S,6R)-4,5,6-tribenzoyloxyoxan-2-yl]methyl benzoate 在 吡啶 、 sodium methylate 、 苄胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 20.0h， 生成 2,3,6-tri-O-acetyl-4-deoxy-D-lyxo-hexose
  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
• 作为产物：
  描述：

  1,2,3,6-四-O-苯甲酰基-alpha-D-甘露糖 在 1,1′-硫代羰基二-2(1H)-吡啶酮 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以54%的产率得到[(2S,4S,5S,6R)-4,5,6-tribenzoyloxyoxan-2-yl]methyl benzoate
  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

文献信息

• PROCESS FOR PREPARING MANNOSE DERIVATIVES
  申请人：ENTEROME

  公开号：US20210309682A1

  公开（公告）日：2021-10-07

  The invention relates to a process to prepare a compound of the following formula (I): (I), in which P represents a protective group of a hydroxyl function which is a —COR 1 group with R 1 representing an aryl or a (C 1 C 6 )alkyl, R represents a hydrogen atom or a protective group of a terminal alkyne, from mannose, comprising the following steps: (a) protecting the 5 hydroxyl groups of the mannose by a protective group P; (b) coupling the protected mannose obtained at step (a) with a compound of the following formula (II). The present invention also relates to a compound of formula (IIIa).