D-gluco-2,3,4,5-tetramethoxyhexanedial | 151909-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-gluco-2,3,4,5-tetramethoxyhexanedial
• CAS: 151909-85-2
• 化学式: C₁₀H₁₈O₆
• 分子量: 234.249
• InChiKey: IIZXZKWDUNCFMF-UTINFBMNSA-N

物化性质

• 沸点：
  320.3±42.0 °C(predicted)
• 密度：
  1.088±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

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：

  D-gluco-2,3,4,5-tetramethoxyhexanedial 在 (-)-(S)-alpine-borane 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (E)-2,3,4,5-tetra-O-methyl-D-gulose 2,4-dinitrophenylhydrazone
  参考文献：
  名称：

  Ward, Dale E.; Liu, YaDong; Rhee, Chung K., Canadian Journal of Chemistry, 1994, vol. 72, # 6, p. 1429 - 1446

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,5-tetra-O-methyl-D-galactitol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.92h， 生成 D-gluco-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