(1S,2R,3R,4R,5R,6S)-3,4,5,6-tetrakis(phenylmethoxy)cyclohexane-1,2-diol | 1607827-99-5

• 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: (1S,2R,3R,4R,5R,6S)-3,4,5,6-tetrakis(phenylmethoxy)cyclohexane-1,2-diol
• CAS: 1607827-99-5
• 化学式: C₃₄H₃₆O₆
• 分子量: 540.656
• InChiKey: VQNWAWRYJQHLAV-ISDDUXATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  40.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R,4R,5R,6S)-3,4,5,6-tetrakis(phenylmethoxy)cyclohexane-1,2-diol 在 氢气 、 palladium dichloride 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以17 mg的产率得到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 、 吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 17.0h， 生成 (1S,2R,3R,4R,5R,6S)-3,4,5,6-tetrakis(phenylmethoxy)cyclohexane-1,2-diol
  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

• BRUZIK, KAROL S.;SALAMONCZYK, GRZEGORZ M., CARBOHYDR. RES., 195,(1989) N, C. 67-73
  作者：BRUZIK, KAROL S.、SALAMONCZYK, GRZEGORZ M.

  DOI：——

  日期：——