((1S,2R)-1,2,3-Trihydroxy-propyl)-phosphonic acid | 88497-20-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: ((1S,2R)-1,2,3-Trihydroxy-propyl)-phosphonic acid
• 英文别名: (S,r)-1,2,3-trihydroxypropylphosphonic acid；[(1S,2R)-1,2,3-trihydroxypropyl]phosphonic acid
• CAS: 88497-20-5
• 化学式: C₃H₉O₆P
• 分子量: 172.075
• InChiKey: CRSOIYXNFFSUFD-GBXIJSLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  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

文献信息

• 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.