(+)-(1R,2S)-1-amino-2-(hydroxymethyl)cyclopropylphosphonic acid | 1253573-40-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: (+)-(1R,2S)-1-amino-2-(hydroxymethyl)cyclopropylphosphonic acid
• 英文别名: [(1R,2S)-1-amino-2-(hydroxymethyl)cyclopropyl]phosphonic acid
• CAS: 1253573-40-8
• 化学式: C₄H₁₀NO₄P
• 分子量: 167.101
• InChiKey: LTSGCTAMEWPMAE-IUYQGCFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  104
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl (+)-(1R,2S)-1-(diethoxyphosphoryl)-2-(hydroxymethyl)cyclopropylcarbamate 在 三甲基溴硅烷 、 乙醇 、 methyloxirane 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 以95%的产率得到(+)-(1R,2S)-1-amino-2-(hydroxymethyl)cyclopropylphosphonic acid
  参考文献：
  名称：

  An efficient approach to the synthesis of enantiomerically pure trans-1-amino-2-(hydroxymethyl)cyclopropanephosphonic acids

  摘要：

  The synthesis of (1R,2S)- and (1S,2R)-1-amino-2-(hydroxymethyl)cyclopropanephosphonic acids was accomplished using different strategies. The (1R,2S)-stereoisomer could be efficiently obtained by the cyclopropanation of ethyl diethoxyphosphorylacetate with the cyclic sulfate derived from (S)-3-benzyloxy-1,2-propandiol as a key step. The (1S,2R)-stereoisomer was synthesized from a readily available (1S,5R)-3-oxabicyclo[3.1.0]hexan-2-on-1-phosphonate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.017

文献信息

• Lewis Acid-Promoted [2 + 1] Cycloaddition Reactions of a 1-Seleno-2-silylethene to 2-Phosphonoacrylates:  Stereoselective Synthesis of a Novel Functionalized α-Aminocyclopropanephosphonic Acid
  作者：Shoko Yamazaki、Takashi Takada、Tomomi Imanishi、Yumiko Moriguchi、Shinichi Yamabe

  DOI：10.1021/jo9805450

  日期：1998.8.1

  Stereoselective SnCl(4)-promoted [2 + 1] cycloaddition reactions of 1-seleno-2-silylethene 1 with 2-phosphonoacrylates 2 lead to highly functionalized cyclopropanephosphonate esters 3 in high yields. The cyclopropane products 3 are potentially versatile starting materials for biologically important compounds. Stereoselective synthesis of a novel functionalized alpha-aminophosphonic acid derivative

  1-硒基-2-甲硅烷基乙烯1与2-膦酰基丙烯酸酯2的立体选择性SnCl（4）促进[2 +1]环加成反应以高收率产生高度官能化的环丙烷膦酸酯3。环丙烷产物3是生物上重要的化合物的潜在通用原料。从环加合物3b实现了立体选择性合成新型的官能化的α-氨基膦酸衍生物，其为（Z）-2，3-甲氨基高丝氨酸13的类似物。通过考虑2-SnCl（4）复杂的结构解释了[2 +1]环加成中的立体选择性。