(R)-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-oxoethyl]phosphonic acid dimethyl ester | 121998-80-9

• 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: (R)-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-oxoethyl]phosphonic acid dimethyl ester
• 英文别名: dimethyl 2,3-O-isopropylidene-D-glyceroylmethylphosphonate；2-dimethoxyphosphoryl-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanone
• CAS: 121998-80-9
• 化学式: C₉H₁₇O₆P
• 分子量: 252.204
• InChiKey: QEDUANKBUNERNA-MRVPVSSYSA-N

物化性质

• 沸点：
  334.3±42.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-oxoethyl]phosphonic acid dimethyl ester 在 palladium dihydroxide 氢气 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 甲醇 、 乙腈 为溶剂， 20.0 ℃ 、607.95 kPa 条件下， 反应 84.0h， 生成 (2S)-2-(tert-butoxycarbonylamino)-8-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-8-oxooctanoic acid
  参考文献：
  名称：

  Synthesis of 2-Amino-8-oxodecanoic Acids (Aodas) Present in Natural Hystone Deacetylase Inhibitors

  摘要：

  Differently substituted 2-amino-8-oxodecanoic acids (Aodas), present in naturally occurring inhibitors of hystone deacetylase (HDAC), have been prepared using a convergent approach. The configuration in position 2 was derived from enantiomerically pure allylglycine or glutamic acid, whereas the stereochemistry of the substituent in position 9 derived from lactic acid or glyceraldehyde derivatives. Starting from allylglycine, (S)-Aodas, protected at the nitrogen as Boc or Fmoc, were obtained in four steps in about 30% overall yield. These products have been used to prepare a simplified analogue of a natural cyclic tetrapeptide HDAC inhibitor by SPPS.

  DOI：

  10.1021/jo0518250
• 作为产物：
  描述：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-羧酸甲酯 、 甲基膦酸二甲酯 在 正丁基锂 作用下， 生成 (R)-[2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-oxoethyl]phosphonic acid dimethyl ester
  参考文献：
  名称：

  Horner-Wittig Reaction of Dimethyl 2,3-O-Isopropylidene-D-glyceroylmethylphosphonate and Its Application to the Formal Synthesis of D-erythro-C₁₈-Sphingosine

  摘要：

  二甲基1,2-O-异丙基化- d-甘油甲基膦酸酯被发现能在碳酸铯存在下与醛反应，溶剂为异丙醇。通过这种反应实现了 d-红糖-C18-神经酰胺的形式合成。

  DOI：

  10.1246/cl.1989.335

文献信息

• An Efficient Preparation of Isosteric Phosphonate Analogues of Sphingolipids by Opening of Oxirane and Cyclic Sulfamidate Intermediates with α-Lithiated Alkylphosphonic Esters
  作者：Chaode Sun、Robert Bittman

  DOI：10.1021/jo0487404

  日期：2004.10.1

  group was introduced via regioselective ring-opening reactions of oxirane 12 and cyclic sulfamidate 22 with lithium dialkyl methylphosphonate, affording 13 and 23, respectively. The synthesis of 1 was completed by SN2 displacement of chloromesylate intermediate 14b with azide ion, followed by conversion of the resulting azido group to a NHBoc group and deprotection. The synthesis of 2 was completed by

  d -赤- （2小号，3 - [R，4 ê）-Sphingosine -1-膦酸酯（1），天然存在的鞘氨醇-1-磷酸（等排膦酸酯类似物1A）和d -核糖-phytosphingosine -1-膦酸酯（2），的电子等排膦酸酯类似物d -核糖-phytosphingosine -1-磷酸（2A），合成开始用甲基2,3- ö异亚丙基d -glycerate（4）和d -核糖-phytosphingosine（3）， 分别。从4开始的8个步骤中形成了环氧乙烷12，从3开始的5个步骤中形成了环状氨基磺酸酯22。通过环氧乙烷12和环状氨基磺酸酯22与二烷基甲基膦酸锂的区域选择性开环反应引入膦酸酯基，分别得到13和23。1的合成通过用叠氮化物离子用S N 2置换氯甲磺酸酯中间体14b，然后将所得的叠氮基团转化为NHBoc基团并脱保护而完成。合成2通过切割缩醛，N-苄基和烷基膦酸酯基团完成。
• Synthesis of Enantiopure 7-Substituted Azepane-2-carboxylic Acids as Templates for Conformationally Constrained Peptidomimetics
  作者：Elena Cini、Giuseppe Bifulco、Gloria Menchi、Manuela Rodriquez、Maurizio Taddei

  DOI：10.1002/ejoc.201101387

  日期：2012.4

  The introduction of a cyclic amino acid in a peptide is one of the best methods to rigidify a strand. A general approach towards a new class of seven-membered ring amino acids is described starting from (S)-tribenzyl glutamic acid γ-aldehyde, which reacts with β-keto phosphonates to generate the Horner–Wadsworth–Emmons product. In the presence of H2 and a Pd catalyst, a four-step process occurs involving

  在肽中引入环状氨基酸是刚性链的最佳方法之一。从 (S)-三苄基谷氨酸 γ-醛开始描述了一种新的七元环氨基酸的一般方法，它与 β-酮膦酸酯反应生成霍纳-沃兹沃思-埃蒙斯产物。在 H2 和 Pd 催化剂存在下，发生四步过程，包括双键加氢、三个苄基保护基的氢解、亚胺形成和还原胺化，以产生良好的 7-取代氮杂环庚烷羧酸。
• Synthesis of an orthogonally protected d-(+)-erythro-sphingosine
  作者：Joseph M Gargano、Watson J Lees

  DOI：10.1016/s0040-4039(01)01152-2

  日期：2001.8

  The synthesis presented provides rapid access to an orthogonally protected d-(+)-erythro-sphingosine: 1-methoxymethyl, 2-azido, 3-benzoyl. After selective deprotection the resulting sphingosine derivative is suitable for coupling to a wide variety of saccharides or other molecules at either the 1- or 3-position.

  提出的合成提供了快速获得正交保护的d-（+）-赤型-鞘氨醇的途径：1-甲氧基甲基，2-叠氮基，3-苯甲酰基。选择性脱保护后，所得的鞘氨醇衍生物适合于在1-或3-位偶联至多种糖或其他分子。
• A convenient route to enantiomerically pure bicyclo[4.3.0]nonanes from sugar allyltin derivatives
  作者：Sławomir Jarosz、Stanisław Skóra

  DOI：10.1016/s0957-4166(00)00083-5

  日期：2000.4

  Tandem Wittig-type Diels-Alder reactions between sugar derived phosphonates and dienoaldehydes obtained from sugar allyltins lead, with high stereoselectivity, to complex oxygenated perhydroindene derivatives with the trans junction between the five- and six-membered rings. The configuration at the newly created stereogenic centers in such bicyclo[4.3.0] systems may be monitored by the geometry of chiral phosphonates. (C) 2000 Elsevier Science Ltd. All rights reserved.
• YAMANOI, TAKASHI;AKIYAMA, TAKASHI;ISHIDA, EIICHI;ABE, HIROYUKI;AMEMIYA, M+, CHEM. LETT.,(1989) N, C. 335-336
  作者：YAMANOI, TAKASHI、AKIYAMA, TAKASHI、ISHIDA, EIICHI、ABE, HIROYUKI、AMEMIYA, M+

  DOI：——

  日期：——