(2R,3R,4R,5R,6R)-2-(acetoxymethyl)-5-(2-oxopropyl)-6-(phosphonooxy)tetrahydro-2H-pyran-3,4-diyl diacetate | 1178931-90-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-5-(2-oxopropyl)-6-(phosphonooxy)tetrahydro-2H-pyran-3,4-diyl diacetate
• CAS: 1178931-90-2
• 化学式: C₁₅H₂₃O₁₂P
• 分子量: 426.314
• InChiKey: VOUPADCIYBRNMR-ARILJUKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.16
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  171.96
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-5-(2-oxopropyl)-6-(phosphonooxy)tetrahydro-2H-pyran-3,4-diyl diacetate 、 N,N'-二环己基-4-吗啉甲脒-5'-O-[羟基(4-吗啉基)磷酰]尿苷(1:1) 在 吡啶 、 四氮唑 作用下， 反应 72.0h， 生成
  参考文献：
  名称：

  Improved synthesis of UDP-2-(2-ketopropyl)galactose and a first synthesis of UDP-2-(2-ketopropyl)glucose for the site-specific linking of biomolecules via modified glycan residues using glycosyltransferases

  摘要：

  The potential of wild-type and mutant glycosyltransferases to produce glycoconjugates carrying sugar moieties with chemical handles has made it possible to conjugate biomelecules with orthogonal reacting groups at specific sites. The synthesis of UDP-2-(2-ketopropyl)galactose has been previously carried out, albeit with difficulty and low efficiency. A modified approach has been developed for the synthesis of UDP-2-(2-ketopropyl)glucose and UDP-2-(2-ketopropyl)galactose, allowing better access to the desired test compounds, the UDP-2-(2-ketopropyl)glucose and UDP-2-(2-ketopropyl)galactose analogs were synthesized in eight steps and 4.8% and 5.3% overall yield, respectively, an improvement over the first generation synthesis involving eight steps and an overall yield of 0.7%. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.01.081
• 作为产物：
  描述：

  C₃₀H₃₇O₁₀P 在 三辛胺 、 palladium 10% on activated carbon 、 氢气 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-5-(2-oxopropyl)-6-(phosphonooxy)tetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  Improved synthesis of UDP-2-(2-ketopropyl)galactose and a first synthesis of UDP-2-(2-ketopropyl)glucose for the site-specific linking of biomolecules via modified glycan residues using glycosyltransferases

  摘要：

  The potential of wild-type and mutant glycosyltransferases to produce glycoconjugates carrying sugar moieties with chemical handles has made it possible to conjugate biomelecules with orthogonal reacting groups at specific sites. The synthesis of UDP-2-(2-ketopropyl)galactose has been previously carried out, albeit with difficulty and low efficiency. A modified approach has been developed for the synthesis of UDP-2-(2-ketopropyl)glucose and UDP-2-(2-ketopropyl)galactose, allowing better access to the desired test compounds, the UDP-2-(2-ketopropyl)glucose and UDP-2-(2-ketopropyl)galactose analogs were synthesized in eight steps and 4.8% and 5.3% overall yield, respectively, an improvement over the first generation synthesis involving eight steps and an overall yield of 0.7%. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.01.081