1,4-ditosyl-2,3-O-isopropylidene erythritol | 190258-23-2

• 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: 1,4-ditosyl-2,3-O-isopropylidene erythritol
• 英文别名: [(4S,5R)-2,2-dimethyl-5-[(4-methylphenyl)sulfonyloxymethyl]-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate
• CAS: 190258-23-2
• 化学式: C₂₁H₂₆O₈S₂
• 分子量: 470.565
• InChiKey: KPFDKWNWYAXRNJ-BGYRXZFFSA-N

物化性质

• 沸点：
  608.3±40.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,4-ditosyl-2,3-O-isopropylidene erythritol 在 盐酸 作用下， 以 甲醇 为溶剂， 以97%的产率得到1,4-bis-O-tosyl-meso-erythritol
  参考文献：
  名称：

  手性羟基硫杂环戊烷的合成作为羰基化合物不对称有机锌加成的潜在催化剂

  摘要：

  旋光性 3-羟基硫杂环戊烷由 L-天冬氨酸立体定向合成，氧化得到两种非对映体 S-氧化物，通过色谱分离并确定其构型。以天然(+)-(R,R)-酒石酸为原料，首次立体定向合成了C2-对称反式-(R,R)-3,4-二羟基硫杂环戊烷。还获得并表征了其一些单官能化衍生物及其 S-氧化物。以类似的方式从内消旋酒石酸中获得内消旋-顺-3,4-二羟基硫杂环戊烷，并通过脂肪酶促进的乙酰化或相应的 O,O'-二乙酰衍生物的水解进行去对称化，得到手性单乙酸酯ee 高达 36%。氧化后得到两种非对映体亚砜，通过色谱法将其分离。对晶体进行 X 射线分析，确定其绝对构型为 1S、3S、4R。所有光学活性产物都被检查为二乙基锌不对称加成到苯甲醛的潜在催化剂。然而，它们被证明具有非常低的催化活性：产物的产率在 10-90% 的范围内，但 ee 仅高达 10%。得出的结论是，在这种类型的反应中，羟基硫化物（亚砜）部分既不

  DOI：

  10.1002/hc.20076
• 作为产物：
  描述：

  Erythritol 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 反应 16.0h， 以94%的产率得到1,4-ditosyl-2,3-O-isopropylidene erythritol
  参考文献：
  名称：

  Stereodependent Fusion and Fission of Vesicles:  Calcium Binding of Synthetic Gemini Phospholipids Containing Two Phosphate Groups

  摘要：

  Three different stereoisomers of a phosphatidic acid analog bearing two phosphate groups have been synthesized from tartaric acid and erythritol. The obtained diastereomeric gemini surfactants differ in their aggregation behavior due to the different spatial orientations of their functional groups. The most remarkable difference in aggregation behavior is encountered when calcium ions are added to vesicle suspensions of the respective isomers. The vesicles formed from the (S,S) and (R,R) isomer undergo fusion, whereas those of the (R,S) isomer show vesicle fission. This remarkable behavior can be explained by a change in the molecular packing of the lipid molecules upon the complexation with calcium ions. An analysis of physical data obtained prior to and after the addition of the calcium ions reveals that the head groups of the diastereomeric surfactants respond differently to these ions: those of the (S,S) isomer increase in size, whereas those of the (R,S) isomer decrease in size. This phenomenon accounts for occurrence of fusion and fission of the vesicles, respectively.

  DOI：

  10.1021/ja962303s

文献信息

• PETERSEN, U.;STADLER, P.;LOCKHOFF, O.;ZELLER, H. -J.;METZGER, K.
  作者：PETERSEN, U.、STADLER, P.、LOCKHOFF, O.、ZELLER, H. -J.、METZGER, K.

  DOI：——

  日期：——
• Stereodependent Fusion and Fission of Vesicles:  Calcium Binding of Synthetic Gemini Phospholipids Containing Two Phosphate Groups
  作者：N. A. J. M. Sommerdijk、T. H. L. Hoeks、M. Synak、M. C. Feiters、R. J. M. Nolte、B. Zwanenburg

  DOI：10.1021/ja962303s

  日期：1997.5.1

  Three different stereoisomers of a phosphatidic acid analog bearing two phosphate groups have been synthesized from tartaric acid and erythritol. The obtained diastereomeric gemini surfactants differ in their aggregation behavior due to the different spatial orientations of their functional groups. The most remarkable difference in aggregation behavior is encountered when calcium ions are added to vesicle suspensions of the respective isomers. The vesicles formed from the (S,S) and (R,R) isomer undergo fusion, whereas those of the (R,S) isomer show vesicle fission. This remarkable behavior can be explained by a change in the molecular packing of the lipid molecules upon the complexation with calcium ions. An analysis of physical data obtained prior to and after the addition of the calcium ions reveals that the head groups of the diastereomeric surfactants respond differently to these ions: those of the (S,S) isomer increase in size, whereas those of the (R,S) isomer decrease in size. This phenomenon accounts for occurrence of fusion and fission of the vesicles, respectively.
• Synthesis of chiral hydroxythiolanes as potential catalysts for asymmetric organozinc additions to carbonyl compounds
  作者：Piotr Kie?basi?ski、Ma?gorzata Albrycht、Marian Miko?ajczyk、Micha? W. Wieczorek、Wies?aw R. Majzner、Agnieszka Filipczak、Piotr Cio?kiewicz

  DOI：10.1002/hc.20076

  日期：——

  give a chiral monoacetate with ee up to 36%. After its oxidation two diastereomeric sulfoxides were obtained which were separated by chromatography. The crystalline one was subjected to X-ray analysis and its absolute configuration was determined as 1S, 3S, 4R. All the optically active products were checked as potential catalysts for asymmetric addition of diethylzinc to benzaldehyde. However, they

  旋光性 3-羟基硫杂环戊烷由 L-天冬氨酸立体定向合成，氧化得到两种非对映体 S-氧化物，通过色谱分离并确定其构型。以天然(+)-(R,R)-酒石酸为原料，首次立体定向合成了C2-对称反式-(R,R)-3,4-二羟基硫杂环戊烷。还获得并表征了其一些单官能化衍生物及其 S-氧化物。以类似的方式从内消旋酒石酸中获得内消旋-顺-3,4-二羟基硫杂环戊烷，并通过脂肪酶促进的乙酰化或相应的 O,O'-二乙酰衍生物的水解进行去对称化，得到手性单乙酸酯ee 高达 36%。氧化后得到两种非对映体亚砜，通过色谱法将其分离。对晶体进行 X 射线分析，确定其绝对构型为 1S、3S、4R。所有光学活性产物都被检查为二乙基锌不对称加成到苯甲醛的潜在催化剂。然而，它们被证明具有非常低的催化活性：产物的产率在 10-90% 的范围内，但 ee 仅高达 10%。得出的结论是，在这种类型的反应中，羟基硫化物（亚砜）部分既不