4-carboxythiobutyric acid S-{[di-(4-chlorophenyl)phosphanyl]methyl}ester | 866363-68-0

• 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: 4-carboxythiobutyric acid S-{[di-(4-chlorophenyl)phosphanyl]methyl}ester
• 英文别名: 5-[Bis(4-chlorophenyl)phosphanylmethylsulfanyl]-5-oxopentanoic acid
• CAS: 866363-68-0
• 化学式: C₁₈H₁₇Cl₂O₃PS
• 分子量: 415.277
• InChiKey: MEEZSXQSYXJKJC-UHFFFAOYSA-N

物化性质

• 沸点：
  542.1±50.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-carboxythiobutyric acid S-{[di-(4-chlorophenyl)phosphanyl]methyl}ester 、 2-叠氮乙基-2-乙酰氨基-2-脱氧-Β-D-吡喃葡萄糖苷 以 水 、 乙腈 为溶剂， 反应 96.0h， 以37%的产率得到4-[2-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethylcarbamoyl]-butyric acid
  参考文献：
  名称：

  On the Preparation of Carbohydrate−Protein Conjugates Using the Traceless Staudinger Ligation

  摘要：

  The nature of a linker used for preparing glycoconjugate vaccines is of utmost importance as it may lead to immunogenic biomolecules. We report the conjugation of carbohydrate haptens to protein carriers leading to potential vaccines using the traceless Staudinger ligation. The ligation relies on the selective transfer of a phosphane substituent to an azide to form a native amide bond in the final product upon release of an oxidized phosphane byproduct. We designed new phosphino-functionalized cross-linkers suitable for protein carrier derivatization. We evaluated their utility in preparing conjugates using both synthetic and purified bacterial carbohydrates. The use of a borane-protected phosphane which is deprotected at the time of the ligation reaction led to the best results observed thus far in terms of stability toward oxidation and reactivity.

  DOI：

  10.1021/jo0505472
• 作为产物：
  描述：

  4-氯苯基溴化镁 在 三氯硅烷 、 sodium methylate 作用下， 以 四氢呋喃 、 乙醚 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 98.33h， 生成 4-carboxythiobutyric acid S-{[di-(4-chlorophenyl)phosphanyl]methyl}ester
  参考文献：
  名称：

  On the Preparation of Carbohydrate−Protein Conjugates Using the Traceless Staudinger Ligation

  摘要：

  The nature of a linker used for preparing glycoconjugate vaccines is of utmost importance as it may lead to immunogenic biomolecules. We report the conjugation of carbohydrate haptens to protein carriers leading to potential vaccines using the traceless Staudinger ligation. The ligation relies on the selective transfer of a phosphane substituent to an azide to form a native amide bond in the final product upon release of an oxidized phosphane byproduct. We designed new phosphino-functionalized cross-linkers suitable for protein carrier derivatization. We evaluated their utility in preparing conjugates using both synthetic and purified bacterial carbohydrates. The use of a borane-protected phosphane which is deprotected at the time of the ligation reaction led to the best results observed thus far in terms of stability toward oxidation and reactivity.

  DOI：

  10.1021/jo0505472

文献信息

• On the Preparation of Carbohydrate−Protein Conjugates Using the Traceless Staudinger Ligation
  作者：Cyrille Grandjean、Alain Boutonnier、Catherine Guerreiro、Jean-Michel Fournier、Laurence A. Mulard

  DOI：10.1021/jo0505472

  日期：2005.9.1

  The nature of a linker used for preparing glycoconjugate vaccines is of utmost importance as it may lead to immunogenic biomolecules. We report the conjugation of carbohydrate haptens to protein carriers leading to potential vaccines using the traceless Staudinger ligation. The ligation relies on the selective transfer of a phosphane substituent to an azide to form a native amide bond in the final product upon release of an oxidized phosphane byproduct. We designed new phosphino-functionalized cross-linkers suitable for protein carrier derivatization. We evaluated their utility in preparing conjugates using both synthetic and purified bacterial carbohydrates. The use of a borane-protected phosphane which is deprotected at the time of the ligation reaction led to the best results observed thus far in terms of stability toward oxidation and reactivity.