diethyl 2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-ethylphosphonate | 201854-47-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl 2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-ethylphosphonate
• 英文别名: diethyl 2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-ethyl phosphonate；Diethyl 2-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)-ethylphosphonate；[(2R,3S,4R,5S,6R)-3,4,5-triacetyloxy-6-(2-diethoxyphosphorylethyl)oxan-2-yl]methyl acetate
• CAS: 201854-47-9
• 化学式: C₂₀H₃₃O₁₂P
• 分子量: 496.449
• InChiKey: CHOMDLXCBWOWJC-SWBPCFCJSA-N

物化性质

• 沸点：
  538.0±40.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  33
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  diethyl 2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-ethylphosphonate 在 吡啶 、 四氮唑 、 三甲基溴硅烷 、 水 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 257.0h， 生成 bis(triethylammonium) [2-(α-D-galactopyranosyl)-ethylphosphono]uridin-5'-yl phosphate
  参考文献：
  名称：

  Non-isosteric C-glycosyl analogues of natural nucleotide diphosphate sugars as glycosyltransferase inhibitors

  摘要：

  A series of C-glycosyl ethylphosphonophosphate analogues of UDP-Glc, UDP-Gal, UDP-GlcNAc and GDP-Fuc were synthesized from the corresponding C-glycosyl ethylphosphonic acids. Analogues were obtained as alpha-anomers through either diastereoselective photo-induced radical addition of glycosyl bromides (D-Glc, D-Gal and L-Fuc) to diethyl vinylphosphonate, or a multi-step sequence (D-GlcNAc), with subsequent coupling with morpholidate-activated nucleotide monophosphates. The in vitro inhibitory activity of UDP-Gal, GDP-Fuc and UDP-GlcNAc analogues towards glycosyltransferases (beta-1,4-Gaff, FUT3 and LgtA) was evaluated through a competition fluorescence assay and IC50 values of 40 mu M, 2 mM and 3.5 mM were obtained, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.057
• 作为产物：
  描述：

  alpha-D-半乳糖 在 三丁基氯化锡 、 氢溴酸 、 sodium cyanoborohydride 、 叔丁醇 作用下， 以 吡啶 、 乙醚 、 溶剂黄146 为溶剂， 反应 116.0h， 生成 diethyl 2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-ethylphosphonate
  参考文献：
  名称：

  [EN] DERIVATIVES OF URIDINE PHOSPHATE AND THEIR USES IN PROTEIN BINDING ASSAYS
  [FR] COMPOSÉS ET LEURS UTILISATIONS DANS DES DOSAGES DE LIAISON AUX PROTÉINES

  摘要：

  公开号：

  WO2011051733A3

文献信息

• Towards α- or β-d-C-glycosyl compounds by tin-catalyzed addition of glycosyl radicals to acrylonitrile and vinylphosphonate, and flexible reduction of tetra-O-acetyl-α-d-glucopyranosyl bromide with cyanoborohydride
  作者：Jean-Pierre Praly、Azin Salek Ardakani、Isabelle Bruyère、Chrystelle Marie-Luce、Bing Bing Qin

  DOI：10.1016/s0008-6215(02)00052-6

  日期：2002.10

  These conditions led to 2-(α- d -manno-, and galactopyranosyl)-ethylphosphonates in 68 and 76% yields. Similarly, radical addition of acetylated 1-bromo-β- d -glucopyranosyl chloride ( 2 ) to acrylonitrile or diethyl vinylphosphonate afforded mainly intermediate chlorides which, upon radical reduction with excess tri- n -butyltin hydride, afforded the corresponding β anomers (40 and 38%, respectively)

  摘要在催化量的氯化三正丁基锡和过量的氰基硼氢化钠（或四正丁基铵）存在下，将乙酰化的α-d-吡喃葡萄糖基溴化物（1）光诱导自由基加成到丙烯腈或乙烯基膦酸二乙酯中，可以高效制备α-构型的壬腈和2-（α-d-吡喃葡萄糖基）-乙基膦酸酯（产率分别为79％和70％）。这些条件导致产率为68％和76％的2-（α-d-甘露糖基和吡喃并吡喃糖基）-乙基膦酸酯。类似地，将乙酰化的1-溴-β-d-吡喃葡萄糖基氯（2）自由基加成到丙烯腈或乙烯基膦酸二乙酯中，主要得到中间体氯化物，在用过量的三正丁基锡氢化物进行自由基还原后，得到相应的β异构体（40和分别由38％的CC和CH键形成。立体控制依赖于d -glycopyranos-1-yl自由基的α-立体选择性猝灭。我们还发现，在叔丁醇中用过量的NaBH 3 CN进行1的紫外光辐照，可得到1,3,4,6-四-O-乙酰基-2-脱氧-α-d-阿拉伯糖-己吡喃糖（结晶后占65％
• The first C-glycosidic analogue of a novel galactosyltransferase inhibitor
  作者：Karine Descroix、Gerd K. Wagner

  DOI：10.1039/c0ob00630k

  日期：——

  Structural analogues and mimics of the natural sugar-nucleotide UDP-galactose (UDP-Gal) are sought after as chemical tools for glycobiology and drug discovery. We have recently developed a novel class of galactosyltransferase (GalT) inhibitors derived from UDP-Gal, bearing an additional substituent at the 5-position of the uracil base. Herein we report the first C-glycosidic derivative of this new

  天然糖核苷酸的结构类似物和模拟物 UDP-半乳糖 （UDP-Gal作为糖生物学和药物发现的化学工具而受到追捧。我们最近开发了一种新型的半乳糖基转移酶（GalT）抑制剂，其衍生自UDP-Gal，在尿嘧啶碱基的5-位带有一个附加的取代基。在本文中，我们报道了这种新型的GalT抑制剂的第一个C-糖苷衍生物。我们描述了新的UDP-C-Gal衍生物的实用收敛合成，包括对自由基化学用于制备半乳糖基乙基膦酸酯（一种关键的合成中间体）的系统研究。新抑制剂在微摩尔浓度下显示出对细菌UDP-Gal 4'-表异构酶的活性。这是碱基修饰的UDP糖作为不是糖基转移酶的UDP糖依赖性酶的抑制剂的第一个例子，因此这些结果可能对将来设计这些酶的抑制剂有影响。
• DERIVATIVES OF URIDINE PHOSPHATE AND THEIR USES IN PROTEIN BINDING ASSAYS
  申请人：Wagner Gerd

  公开号：US20120219963A1

  公开（公告）日：2012-08-30

  The present invention relates to compounds and their use in competitive protein binding assays, for example for use with glycosyl transferase and/or glycoprocessing proteins. The present application also provides kits and apparatuses for use in the assays. In particular, the present invention provides a compound of the formula (I): wherein n is 1, 2 or 3; R 1 is selected from —OH, —OPO 3 H, —OR 4 , —NHR 4 , R 6 ; R 2 and R 3 are each independently selected from —H, —OH, optionally substituted —O-alkyl and —O-alkanoyl; R 4 is selected from an optionally substituted mono or polysaccharide, -alkyl, -alkenyl, -alkynyl, and L-Z, where L is a linking agent and Z is a binding agent; R 6 is an optionally substituted hydrocarbon group; A is either (i) a substituted heteroaryl group, the substituent on the heteroaryl group having a double bond conjugated to the heteroaryl group, or (ii) a substituted aryl group, the substituent on the aryl group having a double bond conjugated to the aryl group.

  本发明涉及化合物及其在竞争性蛋白结合测定中的应用，例如用于糖基转移酶和/或糖基加工蛋白的应用。本申请还提供用于该测定的试剂盒和装置。具体而言，本发明提供式（I）的化合物：其中n为1、2或3；R1选择自—OH、—OPO3H、—OR4、—NHR4、R6；R2和R3各自独立地选择自—H、—OH、可选地取代的—O-烷基和—O-酰基烷基；R4选择自可选地取代的单糖或多糖、-烷基、-烯基、-炔基和L-Z，其中L是连接剂，Z是结合剂；R6是可选地取代的烃基；A是（i）取代的杂环芳基，杂环芳基上的取代基具有共轭到杂环芳基的双键，或（ii）取代的芳基，芳基上的取代基具有共轭到芳基的双键。
• Derivatives of uridine phosphate and their uses in protein binding assays
  申请人：Wagner Gerd

  公开号：US09018370B2

  公开（公告）日：2015-04-28

  The present invention relates to compounds and their use in competitive protein binding assays, for example for use with glycosyl transferase and/or glycoprocessing proteins. The present application also provides kits and apparatuses for use in the assays. In particular, the present invention provides a compound of the formula (I): wherein n is 1, 2 or 3; R1 is selected from —OH, —OPO3H, —OR4, —NHR4, R6; R2 and R3 are each independently selected from —H, —OH, optionally substituted —O-alkyl and —O-alkanoyl; R4 is selected from an optionally substituted mono or polysaccharide, -alkyl, -alkenyl, -alkynyl, and L-Z, where L is a linking agent and Z is a binding agent; R6 is an optionally substituted hydrocarbon group; A is either (i) a substituted heteroaryl group, the substituent on the heteroaryl group having a double bond conjugated to the heteroaryl group, or (ii) a substituted aryl group, the substituent on the aryl group having a double bond conjugated to the aryl group.

  本发明涉及化合物及其在竞争性蛋白质结合测定中的应用，例如用于糖基转移酶和/或糖基加工蛋白质的应用。本申请还提供用于该测定的试剂盒和设备。具体而言，本发明提供了式（I）的化合物：其中n为1、2或3；R1选自—OH、—OPO3H、—OR4、—NHR4、R6；R2和R3各自独立地选自—H、—OH、可选地取代的—O-烷基和—O-酰基烷基；R4选自可选地取代的单糖或多糖、-烷基、-烯基、-炔基和L-Z，其中L是连接剂，Z是结合剂；R6是可选地取代的碳氢基团；A是（i）取代的杂芳基团，杂芳基团上的取代基具有与杂芳基团共轭的双键，或（ii）取代的芳基团，芳基团上的取代基具有与芳基团共轭的双键。
• Diastereoselective synthesis of C-glycosylphosphonates via free-radical glycosylation
  作者：Hans-Dieter Junker、Wolf-Dieter Fessner

  DOI：10.1016/s0040-4039(97)10498-1

  日期：1998.1

  A single step approach for the diastereoselective synthesis of C-glycosidic sugar phosphonates was developed by utilizing a free radical coupling to dialkyl vinylphosphonates to give the title compounds in moderate yield. The method is broadly applicable to sugars, deoxysugars, aminosugars, and oligosaccharides. (C) 1997 Elsevier Science Ltd. All rights reserved.