(2S,3S,4S,5S)-2,3,4,5-tetramethoxyhexanedial | 1004791-97-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5S)-2,3,4,5-tetramethoxyhexanedial
• CAS: 1004791-97-2
• 化学式: C₁₀H₁₈O₆
• 分子量: 234.249
• InChiKey: IIZXZKWDUNCFMF-ZYUZMQFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.56
• 重原子数：
  16.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5S)-2,3,4,5-tetramethoxyhexanedial 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 吡啶 、 sodium tetrahydroborate 、 氢气 、 三乙胺 、 palladium dichloride 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 33.0h， 生成 epi-Inositol
  参考文献：
  名称：

  Synthesis of allo- and epi-Inositol via the NHC-Catalyzed Carbocyclization of Carbohydrate-Derived Dialdehydes

  摘要：

  A synthesis of carbocyclic sugars from carbohydrate-derived dialdehydes using organocatalysis has been developed. Sorbitol, mannitol, and galactitol were converted via 1,6-tritylation, perbenzylation or permethylation, detritylation, and Swern oxidation into 2,3,4,5-tetra-O-alkyl-dialdoses that were cyclized via the benzoin reaction promoted by a triazolium carbene. Manno- and galacto-configured dialdehydes gave predominantly single inosose stereoisomers in up to 75% yield if the mixture was acetylated prior to isolation while the gluco-dialdehyde afforded a mixture of three stereoisomers in 61% overall yield. The inososes were stereospecifically reduced using sodium borohydride and then deprotected to give allo- and epi-inositol in good yield that confirmed the structural and stereochemical assignments.

  DOI：

  10.1021/jo500645z
• 作为产物：
  描述：

  2,3,4,5-tetra-O-methyl-1,6-di-O-trityl-D-mannitol 在 草酰氯 、 对甲苯磺酸 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.92h， 生成 (2S,3S,4S,5S)-2,3,4,5-tetramethoxyhexanedial
  参考文献：
  名称：

  Synthesis of allo- and epi-Inositol via the NHC-Catalyzed Carbocyclization of Carbohydrate-Derived Dialdehydes

  摘要：

  A synthesis of carbocyclic sugars from carbohydrate-derived dialdehydes using organocatalysis has been developed. Sorbitol, mannitol, and galactitol were converted via 1,6-tritylation, perbenzylation or permethylation, detritylation, and Swern oxidation into 2,3,4,5-tetra-O-alkyl-dialdoses that were cyclized via the benzoin reaction promoted by a triazolium carbene. Manno- and galacto-configured dialdehydes gave predominantly single inosose stereoisomers in up to 75% yield if the mixture was acetylated prior to isolation while the gluco-dialdehyde afforded a mixture of three stereoisomers in 61% overall yield. The inososes were stereospecifically reduced using sodium borohydride and then deprotected to give allo- and epi-inositol in good yield that confirmed the structural and stereochemical assignments.

  DOI：

  10.1021/jo500645z