dimethyl (R)-hydroxy-[(2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]methylphosphonate | 1255097-18-7

• 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: dimethyl (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]-[dimethoxy(oxido)phosphaniumyl]methanol
• CAS: 1255097-18-7
• 化学式: C₁₁H₂₃O₈P
• 分子量: 314.273
• InChiKey: LVKGRJNMLUBSQN-GWOFURMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  亚磷酸二甲酯 、 (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7%的产率得到dimethyl (R)-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

• Stereochemistry of the Three-Component Reaction Between the Ley′S Aldehyde, Benzyl Amines, and Trialkyl Phosphites. A New Approach to the Protected Enantiomerically Pure 1-Amino-2,3-Dihydroxypropylphosphonates
  作者：Dorota G. Piotrowska、Iwona E. Głowacka、Andrzej E. Wróblewski

  DOI：10.1080/10426507.2014.883624

  日期：2014.8.3

  three-component reaction between trimethyl phosphite, (2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2-carbaldehyde (Ley’s aldehyde), and benzhydrylamine. Since both aminophosphonates 10 exist in a chloroform solution as single rotamers, the absolute configurations at C1′ were unequivocally established based on 1H and 13C NMR spectral data. Studies on stereochemistry of the addition of trialkyl phosphites

  摘要 对映体纯正交保护的二甲基 1-氨基膦酸酯 (2R,5R,6R,1'R)- 和 (2R,5R,6R,1'S)-10，4-羟基苏氨酸的膦酸酯类似物，采用三组分制备。亚磷酸三甲酯、(2R,5R,6R)-5,6-二甲氧基-5,6-二甲基-1,4-二恶烷-2-甲醛（莱氏醛）和二苯甲基胺之间的反应。由于两种氨基膦酸酯 10 均以单一旋转异构体的形式存在于氯仿溶液中，因此基于 1H 和 13C NMR 光谱数据明确确定了 C1' 处的绝对构型。对亚磷酸三烷基酯加成的立体化学研究表明，在所有情况下，在氯仿中，亲核试剂优先攻击 C˭N 键的 si 面，而在醇中，1,2-立体诱导可以忽略不计，苯乙胺的手性和手性感是 1,3-不对称诱导中 π 面辨别的唯一原因。图形概要
• 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.