(2S,3S,4R,5R,6R)-6-hydroxy-2,3,4,5-tetramethoxycyclohexanone | 1607827-86-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5R,6R)-6-hydroxy-2,3,4,5-tetramethoxycyclohexanone
• CAS: 1607827-86-0
• 化学式: C₁₀H₁₈O₆
• 分子量: 234.249
• InChiKey: VPWKJVFUNUULSD-BOHATCBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.01
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R,6R)-6-hydroxy-2,3,4,5-tetramethoxycyclohexanone 在 吡啶 、 sodium tetrahydroborate 、 氢气 、 palladium dichloride 作用下， 以 乙醇 为溶剂， 反应 17.0h， 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：

  (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 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以62%的产率得到(2S,3S,4R,5R,6R)-6-hydroxy-2,3,4,5-tetramethoxycyclohexanone
  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

文献信息

• Nucleophilic Trapping of Alkoxy-Stabilized Oxyallyl Systems Generated from Inosose 2-O-Mesylates
  作者：Ben Greatrex、Kieran Stockton、Stephen Glover

  DOI：10.1055/s-0034-1379490

  日期：——

  Protected inosose 2-O-mesylates generate oxyallyl systems by elimination of the mesylate group after enolization. The reaction is promoted by weak bases such as triethylamine and azide, and the oxyallyl systems are then trapped by nucleophilic alcohols or azide. Computations using DFT/B3LYP confirm that the singlet planar oxyallyl is stabilized by the exocyclic alkoxy group.