2,3:5,6-di-O-isopropylidene-2-C-methyl-L-gulono-1,4-lactone | 1072905-62-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3:5,6-di-O-isopropylidene-2-C-methyl-L-gulono-1,4-lactone
• CAS: 1072905-62-4
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: GRWXMIGCVRUFNZ-ZZIUEJKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.97
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,3:5,6-di-O-isopropylidene-2-C-methyl-L-gulono-1,4-lactone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 19.0h， 以70%的产率得到2,3:5,6-di-O-isopropylidene-2-C-methyl-L-gulitol
  参考文献：
  名称：

  Green syntheses of new 2-C-methyl aldohexoses and 5-C-methyl ketohexoses: d-tagatose-3-epimerase (DTE)—a promiscuous enzyme

  摘要：

  The Kiliani synthesis oil the 4 readily accessible ketohexoses (D-fructose, D-tagatose, L-sorbose, D-psicose) allows access to 4 diastereomeric 2-C-methyl-aldohexoses (2-C-methyl-D-mannose, 2-C-methyl-D-talose, 2-C-methyl-L-gulose, 2-C-methyl-D-allose) and 4 diastereomeric 2-C-methyl-alditols (2-C-methyl-mannitol, 2-C-methyl-D-talitol, 2-C-methyl-L-gulitol, 2-C-methyl-D-allitol). Microbial oxidation of 2-C-methyl-D-mannitol and 2-C-metllyl-L-gulitol gave 5-C-methyl-D-fructose; Microbial oxidation of 2-C-methyl-D-talitol afforded 5-C-methyl-D-psicose, whereas 2-C-methyl-D-allitol formed 5-C-methyl-Lpsicose. Both enantiomers of 5-C-methyl-fructose were equilibrated by D-tagatose-3-epimerase (DTE) with both enantiomers of 5-C-methyl-psicose. These transformations demonstrate that polyol dehydrogenases and DTE act on branched synthetic sugars. Full NMR analyses show that 5-C-methyl-D-fructose is present as the P-pyranose and P-furanose forms in a ratio of 90:10; all pyranose and furanose forms of 5-C-methyl-D-psicose are present in solution. The combination of chemical and biological procedures allows the environmentally friendly generation of a new family of branched monosaccharides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.034
• 作为产物：
  描述：

  2-C-iodomethyl-2,3:5,6-di-O-isopropylidene-L-gulono-1,4-lactone 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 17.0h， 以98%的产率得到2,3:5,6-di-O-isopropylidene-2-C-methyl-L-gulono-1,4-lactone
  参考文献：
  名称：

  Green syntheses of new 2-C-methyl aldohexoses and 5-C-methyl ketohexoses: d-tagatose-3-epimerase (DTE)—a promiscuous enzyme

  摘要：

  The Kiliani synthesis oil the 4 readily accessible ketohexoses (D-fructose, D-tagatose, L-sorbose, D-psicose) allows access to 4 diastereomeric 2-C-methyl-aldohexoses (2-C-methyl-D-mannose, 2-C-methyl-D-talose, 2-C-methyl-L-gulose, 2-C-methyl-D-allose) and 4 diastereomeric 2-C-methyl-alditols (2-C-methyl-mannitol, 2-C-methyl-D-talitol, 2-C-methyl-L-gulitol, 2-C-methyl-D-allitol). Microbial oxidation of 2-C-methyl-D-mannitol and 2-C-metllyl-L-gulitol gave 5-C-methyl-D-fructose; Microbial oxidation of 2-C-methyl-D-talitol afforded 5-C-methyl-D-psicose, whereas 2-C-methyl-D-allitol formed 5-C-methyl-Lpsicose. Both enantiomers of 5-C-methyl-fructose were equilibrated by D-tagatose-3-epimerase (DTE) with both enantiomers of 5-C-methyl-psicose. These transformations demonstrate that polyol dehydrogenases and DTE act on branched synthetic sugars. Full NMR analyses show that 5-C-methyl-D-fructose is present as the P-pyranose and P-furanose forms in a ratio of 90:10; all pyranose and furanose forms of 5-C-methyl-D-psicose are present in solution. The combination of chemical and biological procedures allows the environmentally friendly generation of a new family of branched monosaccharides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.034