2,3:4,5-Di-O-isopropylidene-1-O-propionyl-β-D-fructopyranose | 76498-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 2,3:4,5-Di-O-isopropylidene-1-O-propionyl-β-D-fructopyranose
• 英文别名: 1-O-<3-Propanoyl>-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose；[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl propanoate
• CAS: 76498-42-5
• 化学式: C₁₅H₂₄O₇
• 分子量: 316.351
• InChiKey: SVTUEOZEXCCIMF-NYMYIZQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3:4,5-Di-O-isopropylidene-1-O-propionyl-β-D-fructopyranose 、 叔丁基二甲基氯硅烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 生成 、
  参考文献：
  名称：

  2,3:4,5-DI-O-Isopropylidene-β-d-Fructopyranose as Chiral Auxiliary in Asymmetric α-Alkylation Of Ester Enolates

  摘要：

  The asymmetric alpha-alkylation of enolates of chiral esters derived from 2,3:4,5-di-O-isopropylidene-beta--D-fructopyranose (1) was studied. The diastereoselectivities range from 1:1 to 7:3. The absolute stereochemistry of the major S-isomers were established by chemical correlation. The diastereoselectivities of the alkylated products were similar to those observed in the deprotonation steps. The stereochemical outcome can be interpreted by an intramolecular complexation of the lithium cation of the carbohydrate ester enolates.

  DOI：

  10.1080/07328309608005685
• 作为产物：
  描述：

  蔗糖 在 硫酸 、 三乙胺 作用下， 以 苯 为溶剂， 反应 30.0h， 生成 2,3:4,5-Di-O-isopropylidene-1-O-propionyl-β-D-fructopyranose
  参考文献：
  名称：

  2,3:4,5-DI-O-Isopropylidene-β-d-Fructopyranose as Chiral Auxiliary in Asymmetric α-Alkylation Of Ester Enolates

  摘要：

  The asymmetric alpha-alkylation of enolates of chiral esters derived from 2,3:4,5-di-O-isopropylidene-beta--D-fructopyranose (1) was studied. The diastereoselectivities range from 1:1 to 7:3. The absolute stereochemistry of the major S-isomers were established by chemical correlation. The diastereoselectivities of the alkylated products were similar to those observed in the deprotonation steps. The stereochemical outcome can be interpreted by an intramolecular complexation of the lithium cation of the carbohydrate ester enolates.

  DOI：

  10.1080/07328309608005685

文献信息

• Acyclic stereoselection. 11. Double stereodifferentiation as a method for achieving superior Cram's rule selectivity in aldol condensations with chiral aldehydes
  作者：Clayton H. Heathcock、Charles T. White、James Jeffery Morrison、Don VanDerveer

  DOI：10.1021/jo00320a014

  日期：1981.3