di[(1R,2S,5R)-menthyl] (S,R,)-(1,2,3-trihydroxypropyl)phosphonate | 753454-02-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: di[(1R,2S,5R)-menthyl] (S,R,)-(1,2,3-trihydroxypropyl)phosphonate
• 英文别名: di[(1R,2S,5R)-menthyl] (1S,2R)-1,2,3-trihydroxypropylphosphonate；(1S,2R)-1-bis[[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy]phosphorylpropane-1,2,3-triol
• CAS: 753454-02-3
• 化学式: C₂₃H₄₅O₆P
• 分子量: 448.58
• InChiKey: KFXGXXGUZFFPJV-WNDRFJMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  di[(1R,2S,5R)-menthyl] (S,R,)-(1,2,3-trihydroxypropyl)phosphonate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 ((1S,2R)-1,2,3-Trihydroxy-propyl)-phosphonic acid
  参考文献：
  名称：

  Double and triple asymmetric induction in phosphaaldol reactions

  摘要：

  A multiple asymmetric induction synthesis was applied to increase the stereoselectivity of the phosphaaldol reaction. The double stereoselectivity was achieved in the reaction of chiral di(1R,2S,5R)-menthyl phosphite 3 with chiral 2,3-D-isopropyliden-(R)-aldehyde 2. The reaction of aldehyde 2 with phosphite 1 in the presence of chiral (R)-ALB catalyst proceeding under stereochemical control of three chiral auxiliaries was the most stereoselective to support the conception of multiplicativity of facial selectivities of chiral reactants involved into the reaction. The stereochemistry of the phosphaaldol reaction was in agreement with Cram's rule. The absolute configuration of the new chiral compounds was established on the basis of NMR and X-ray analysis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.05.022
• 作为产物：
  描述：

  hydrogen di[(1R,2S,5R)-menthyl] phosphite 在 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 水 为溶剂， 生成 di[(1R,2S,5R)-menthyl] (S,R,)-(1,2,3-trihydroxypropyl)phosphonate
  参考文献：
  名称：

  Double and triple asymmetric induction in phosphaaldol reactions

  摘要：

  A multiple asymmetric induction synthesis was applied to increase the stereoselectivity of the phosphaaldol reaction. The double stereoselectivity was achieved in the reaction of chiral di(1R,2S,5R)-menthyl phosphite 3 with chiral 2,3-D-isopropyliden-(R)-aldehyde 2. The reaction of aldehyde 2 with phosphite 1 in the presence of chiral (R)-ALB catalyst proceeding under stereochemical control of three chiral auxiliaries was the most stereoselective to support the conception of multiplicativity of facial selectivities of chiral reactants involved into the reaction. The stereochemistry of the phosphaaldol reaction was in agreement with Cram's rule. The absolute configuration of the new chiral compounds was established on the basis of NMR and X-ray analysis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.05.022

文献信息

• Organic catalysis of phospha-aldol condensation
  作者：A. O. Kolodyazhnaya、V. P. Kukhar、O. I. Kolodyazhnyi

  DOI：10.1134/s1070363208110091

  日期：2008.11

  Phospha-aldol reaction of dialkylphosphites with carbonyl compounds is catalyzed by cinchonine alkaloids and thier modified derivatives to give optically active hydroxyphosphonates. The use of diastereomeric pairs of alkaloids allowed obtaining both optical antipodes of hydroxyphosphonates. Cinchonine alkaloids show the highest enantioselectivity as organic catalysts. It was found that ordinary crystallization of some enantiomerically enriched hydroxyphosphonates leads to isolation of the enantiomerically pure stereoisomers. Hydroxyphosphonic acids were obtained by hydrolysis of phosphonates. Fluoroalkylphosphonates were obtained by reaction with diethylaminotrifluorosulfurane (DAST).
• Asymmetric synthesis of phosphathreoninic acid
  作者：A. O. Kolodyazhnaya、V. P. Kukhar’、O. I. Kolodyazhnyi

  DOI：10.1007/s11176-005-0123-3

  日期：2004.12
• Double and triple asymmetric induction in phosphaaldol reactions
  作者：Anastasia O. Kolodiazhna、Valery P. Kukhar、Alexander N. Chernega、Oleg I. Kolodiazhnyi

  DOI：10.1016/j.tetasy.2004.05.022

  日期：2004.7

  A multiple asymmetric induction synthesis was applied to increase the stereoselectivity of the phosphaaldol reaction. The double stereoselectivity was achieved in the reaction of chiral di(1R,2S,5R)-menthyl phosphite 3 with chiral 2,3-D-isopropyliden-(R)-aldehyde 2. The reaction of aldehyde 2 with phosphite 1 in the presence of chiral (R)-ALB catalyst proceeding under stereochemical control of three chiral auxiliaries was the most stereoselective to support the conception of multiplicativity of facial selectivities of chiral reactants involved into the reaction. The stereochemistry of the phosphaaldol reaction was in agreement with Cram's rule. The absolute configuration of the new chiral compounds was established on the basis of NMR and X-ray analysis. (C) 2004 Elsevier Ltd. All rights reserved.