dibenzyl (R)-hydroxy-[(2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]methylphosphonate | 1255097-23-4

• 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: dibenzyl (R)-hydroxy-[(2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]methylphosphonate
• 英文别名: (R)-[(2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]-[oxido-bis(phenylmethoxy)phosphaniumyl]methanol
• CAS: 1255097-23-4
• 化学式: C₂₃H₃₁O₈P
• 分子量: 466.468
• InChiKey: AEKXCWAGVFTVBG-SSGKUCQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  98.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  亚磷酸二苄酯 、 (2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carbaldehyde 在 三乙胺 作用下， 反应 24.0h， 以60%的产率得到dibenzyl (S)-hydroxy-[(2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]methylphosphonate
  参考文献：
  名称：

  New approach to the enantiomerically pure 1,2,3-trihydroxypropylphosphonates

  摘要：

  The replacement of 2,3-O-cyclohexylidene-u-glyceraldehyde with (2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carbaldehyde (Ley's aldehyde) has led to significant improvements in the isolation of both diastereoisomers of the respective 2,3-O-BOA 1,2,3-trihydroxypropylphosphonates. The triethylamine-catalysed addition of dialkyl phosphites and lithium diethyl phosphonate gave the products in moderate (ca. 1:2) diastereoselectivity while the application of diethyl trimethylsilyl phosphite afforded a 1:9 mixture of diethyl (R)- and (S)-hydroxy-[(2R5R,6R)-5,6-dimethoxy-5,6-dimethy11,4-dioxan-2-ylimethylphosphonates. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.031

文献信息

• New approach to the enantiomerically pure 1,2,3-trihydroxypropylphosphonates
  作者：Dorota G. Piotrowska、Iwona E. Głowacka、Andrzej E. Wróblewski

  DOI：10.1016/j.tetasy.2010.06.031

  日期：2010.9

  The replacement of 2,3-O-cyclohexylidene-u-glyceraldehyde with (2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carbaldehyde (Ley's aldehyde) has led to significant improvements in the isolation of both diastereoisomers of the respective 2,3-O-BOA 1,2,3-trihydroxypropylphosphonates. The triethylamine-catalysed addition of dialkyl phosphites and lithium diethyl phosphonate gave the products in moderate (ca. 1:2) diastereoselectivity while the application of diethyl trimethylsilyl phosphite afforded a 1:9 mixture of diethyl (R)- and (S)-hydroxy-[(2R5R,6R)-5,6-dimethoxy-5,6-dimethy11,4-dioxan-2-ylimethylphosphonates. (C) 2010 Elsevier Ltd. All rights reserved.