triethyl <14C>orthoformate | 108055-42-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: triethyl <14C>orthoformate
• 英文别名: diethoxy(114C)methoxyethane
• CAS: 108055-42-1
• 化学式: C₇H₁₆O₃
• 分子量: 150.191
• InChiKey: GKASDNZWUGIAMG-WGGUOBTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-二氯-4,5-嘧啶二胺 、 triethyl <14C>orthoformate 在 甲烷磺酸 、 原甲酸三乙酯 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 <8-14C>-2,6-dichloro-9H-purine
  参考文献：
  名称：

  [8-14C]-2,6-二氯-9H-嘌呤的合成，14C-核苷的放射性标记前体

  摘要：

  描述了 [8- 14 C]-2,6-二氯-9H-嘌呤 (2)（一种用于制备 14 C 标记核苷的放射性标记前体）的合成。[ 14 C] 原甲酸三乙酯与 4,5-二氨基-2,6-二氯嘧啶 (1) 在乙腈中在 90 o C 下与甲磺酸作为催化剂反应，以 84% 的放射化学产率生成 2。2 与 1-O-乙酰基-2,3,5-三-O-苯甲酰基-D-呋喃核糖反应生成[8- 14 C]-9-(2,3,5-三-O-苯甲酰基-β- D-呋喃核糖基)-2,6-二氯嘌呤 (3)，产率为 86%。3的放射化学纯度高于98%，比活度为36 mCi/mmol。该方法普遍适用于药物开发中嘌呤的 14 C-标记

  DOI：

  10.1002/jlcr.2580360509

文献信息

• 10th international symposium on the synthesis and applications of isotopes and isotopically labelled compounds - poster presentations Session 19, Sunday, June 14 to Thursday, June 18, 2009
  作者：William Wheeler

  DOI：10.1002/jlcr.1776

  日期：——

  The poster session is a series of papers dealing with a conglomeration of all of the previous sessions. Cristian Postolache, the fourth of the Wiley Young Scientist Award winners gave a Poster in this session. Copyright © 2010 John Wiley & Sons, Ltd.

  海报展示环节是一系列论文，涵盖了之前所有会议的综合内容。克里斯蒂安·波斯托拉切（Cristian Postolache），作为威利青年科学家奖的第四位获奖者，在此环节呈交了一份海报。版权所有 © 2010 约翰威利父子有限公司。
• The 14C, 13C, and 15N syntheses of a potent VEGFR-2 kinase inhibitor, Brivanib, and its prodrug, Brivanib Alaninate
  作者：Scott B. Tran、Michael W. Lago、Yuan Tian、Sharon X. Gong、Indu Batra、Alban J. Allentoff、Brad D. Maxwell、Samuel J. Bonacorsi、Marc Ogan、J. Kent Rinehart、Balu Balasubramanian

  DOI：10.1002/jlcr.1871

  日期：2011.5.30

  The interruption of tyrosine kinase vascular endothelial growth factor receptor-2 (VEGFR-2) signaling by the binding of a small molecule inhibitor, for example, Brivanib, to VEGFR-2 kinase domain has been shown as an effective method of slowing angiogenesis and tumor progression. [14C]Brivanib, 13 and its prodrug [14C]Brivanib Alaninate, 15 were prepared to support preclinical and clinical studies. Their respective stable isotope-labeled versions, [13CN2]Brivanib, 21 and [13CN2]Brivanib Alaninate, 28, were also prepared to support bioanalytical LC-MS analyses of clinical samples. All of the four title compounds were synthetically derived from the respective isotopically labeled common pyrrolotriazinone intermediate, 6 or 16. This labeled central core pyrrolotriazinone was also conveniently used to synthesize other structurally related drug discovery candidates. Copyright © 2011 John wiley & Sons, Ltd.

  酪氨酸激酶血管内皮生长因子受体-2（VEGFR-2）信号传导的中断，通过小分子抑制剂（例如Brivanib）与VEGFR-2激酶域的结合，已被证明是减缓血管生成和肿瘤进展的有效方法。[14C]Brivanib及其前药[14C]Brivanib Alaninate被制备以支持临床前和临床研究。它们各自的稳定同位素标记版本[13CN2]Brivanib和[13CN2]Brivanib Alaninate也被准备以支持临床样本的生物分析LC-MS分析。所有四种标题化合物都是从各自的同位素标记的常见吡咯三嗪酮中间体合成的。这个标记的中心核心吡咯三嗪酮也方便用于合成其他结构相关的药物发现候选物。版权 © 2011 John Wiley & Sons, Ltd.
• Synthesis of [14C]-radiolabelled entecavir
  作者：Marc D. Ogan、David J. Kucera、Yadagiri R. Pendri、J. Kent Rinehart

  DOI：10.1002/jlcr.955

  日期：2005.8

  Radiolabelled [14C]entecavir, (1), was prepared in 12 steps from (1S,2R,3S,5R)-3-(benzyloxy)-2-(benzyloxymethyl)-6-oxa-bicyclo[3.1.0]hexane 2. The chemical yield of [14C]entecavir was 14% from the epoxide 2. Introduction of [14C] radiolabel was achieved by elaboration of 4,5-diaminopyrimidine 8 with triethyl[14C]orthoformate to purine derivative 9. The radiochemical yield of [14C]entecavir from triethyl[14C]orthoformate was 11.3%. Radiochemical purity of [14C]entecavir determined by HPLC was 99.8%. The specific activity of [14C]entecavir was 108 µCi/mg (29.9 mCi/mmol). Copyright © 2005 John Wiley & Sons, Ltd.

  放射性标记的[14C]恩替卡韦（1）是通过12步从（1S,2R,3S,5R）-3-（苄氧基）-2-（苄氧甲基）-6-氧-双环[3.1.0]己烷2合成的。[14C]恩替卡韦的化学收率为14%，来自环氧化物2。通过将4,5-二氨基嘧啶8与三乙基[14C]正腈酸酯反应，获得了嘌呤衍生物9，从而引入了[14C]放射标记。[14C]恩替卡韦从三乙基[14C]正腈酸酯的放射化学收率为11.3%。通过高效液相色谱法（HPLC）测定，[14C]恩替卡韦的放射化学纯度为99.8%。[14C]恩替卡韦的比活性为108 µCi/mg（29.9 mCi/mmol）。版权所有 © 2005 约翰·威利与儿子有限公司。
• Biosynthesis of the isoflavan isomucronulatol: Origin of the 2′,3′,4′-oxygenation pattern
  作者：Hakim A.M. Al-Ani、Paul M. Dewick

  DOI：10.1016/s0031-9422(00)80806-7

  日期：1985.1

  arborescens ) have demonstrated that 7-hydroxy-4′-methoxyisoflavone (formononetin), 7,3′-dihydroxy-4′-methoxyisoflavone (calycosin), 7,2′,3′-trihydroxy-4′-methoxyisoflavone (koparin) and 7,2′-dihydroxy-3′,4′-dimethoxyisoflavone are excellent precursors of (3 R )-isomucronulatol (7,2′-dihydroxy-3′,4′-dimethoxyisoflavan). 7,2′-Dihydroxy- 4′-methoxyisoflavone (2′-hydroxyformononetin) and 7-hydroxy-3′,4′-dimethoxyisoflavone

  摘要 用 14 C-标记的异黄酮喂养番泻叶 (Colutea arborescens) 的幼苗和豆荚的实验表明，7-羟基-4'-甲氧基异黄酮 (formononetin)、7,3'-二羟基-4'-甲氧基异黄酮 (花萼)、 7,2',3'-三羟基-4'-甲氧基异黄酮 (koparin) 和 7,2'-二羟基-3',4'-二甲氧基异黄酮是 (3 R )-isomucronulatol (7,2'-dihydroxy- 3',4'-二甲氧基异黄烷）。然而，7,2'-二羟基-4'-甲氧基异黄酮（2'-羟基甲氧基异黄酮）和7-羟基-3',4'-二甲氧基异黄酮（cladrin）是较差的底物。因此，从芒柄花素到异木糖醇的生物合成顺序包括 3'-羟基化、2'-羟基化和 3'-O-甲基化，然后大概是 7,2'-二羟基-3',4'-二甲氧基异黄酮的立体定向还原。处理 2',3',
• Bhandari, Prabha; Crombie, Leslie; Daniels, Peter, Journal of the Chemical Society. Perkin transactions I, 1992, # 7, p. 839 - 850
  作者：Bhandari, Prabha、Crombie, Leslie、Daniels, Peter、Holden, Ian、Bruggen, Nicholas Van、Whiting, Donald A.

  DOI：——

  日期：——