3-Benzo[1,3]dioxol-5-yl-propionic acid (3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl ester | 174970-67-3

• 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: 3-Benzo[1,3]dioxol-5-yl-propionic acid (3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl ester
• CAS: 174970-67-3
• 化学式: C₂₂H₂₈O₉
• 分子量: 436.459
• InChiKey: NTOJWIGTKWOJBB-GZHDQSLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  90.91
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3-溴丙烯 、 3-Benzo[1,3]dioxol-5-yl-propionic acid (3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl ester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 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 4-二甲氨基吡啶 、 硫酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 54.0h， 生成 3-Benzo[1,3]dioxol-5-yl-propionic acid (3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl ester
  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

• 2,3:4,5-DI-<i>O</i>-Isopropylidene-β-d-Fructopyranose as Chiral Auxiliary in Asymmetric α-Alkylation Of Ester Enolates
  作者：Paulo R.R. Costa、Vitor F. Ferreira、Karla G. Alencar、Hiran C.A. Filho、Claudio M. Ferreira、Sergio Pinheiro

  DOI：10.1080/07328309608005685

  日期：1996.8

  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.