2-methyl-2-thiopseudobiuret hydroiodide | 34277-75-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 2-methyl-2-thiopseudobiuret hydroiodide
• 英文别名: (E)-[amino(methylsulfanyl)methylidene]-carbamoylazanium;iodide
• CAS: 34277-75-3
• 化学式: C₃H₇N₃OS*HI
• 分子量: 261.087
• InChiKey: FHOJLFMQXBUAHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.17
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-2-thiopseudobiuret hydroiodide 以 乙醇 为溶剂， 生成 缩二脲
  参考文献：
  名称：

  Reaction of S-methiodide derivatives of activated thioureas with hydroxylic compounds. Novel synthesis of mercaptans

  摘要：

  DOI：

  10.1021/jo00975a015
• 作为产物：
  描述：

  硫代缩二脲 、 碘甲烷 以 乙腈 为溶剂， 反应 0.5h， 生成 2-methyl-2-thiopseudobiuret hydroiodide
  参考文献：
  名称：

  TAN-1057 A/B 的全合成，一种来自 Flexibacter sp. 的新型二肽抗生素。PK-74

  摘要：

  TAN-1057 (1a, b) - 一种对耐甲氧西林金黄色葡萄球菌具有活性的新型天然二肽抗生素 - 从 Nα、Nδ、Nω-tri-ZL-精氨酸 20b 开始，通过相应的重氮酮 21b 合成。这在光解后重排为烯酮，其被 (±)-2,4,5,6-四氢-5-甲氨基-2-脲基嘧啶-4-一 (3) 捕获，得到完全保护的二肽 23 (30%) . 后者通过氢解脱保护得到最终化合物，为两种差向异构体的混合物 - TAN-1057A，B - 先前从 Flexibacter sp. 菌株中分离。PK-74。中间体3由3-氨基-2-(NZN-甲基氨基)丙酸甲酯盐酸盐(16)和2-甲基-2-硫代伪缩二脲氢碘化物(18)一步制备，产率为35％。

  DOI：

  10.1002/(sici)1099-0690(199805)1998:5<777::aid-ejoc777>3.0.co;2-w

文献信息

• First enantioselective synthesis of the novel antiinfective TAN-1057A via its aminomethyl-substituted dihydropyrimidinone heterocycle
  作者：Vladimir N. Belov、Michael Brands、Siegfried Raddatz、Jochen Krüger、Sofia Nikolskaya、Viktor Sokolov、Armin de Meijere

  DOI：10.1016/j.tet.2004.06.034

  日期：2004.8

  Enantiomerically pure N-2-Z-N-2-MeAsnOH [(S)-14], prepared in 8 steps (23% overall yield) from asparaginic acid, was first subjected to a Hofmann degradation with PhI(OCOCF3)(2) yielding (S)-N-2-Z-N-2-methyl-2,3-diaminopropanoic acid [N-2-Z-N-2-Me-L-A(2)pr, (S)-15], and this in turn was protected to give N-2-Z-N-3-Boc-N-2-Me-L-A(2)pr [(S)-17]. Condensation of (S)-17 with HN=C(SMe)NHCONH2 followed by removal of the tert-butoxycarbonyl protecting group, cyclization and hydrogenolytic removal of the Z-group gave the heterocycle of TAN-1057A [(S)-1] with an e.e. of 87 in 36% yield [from (S)-14]. Coupling of (S)-1 with (S)-tris-Z-beta-homoarginine (20a) in the presence of O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) and iPr(2)NEt in N,N-dimethyl-acetamide followed by hydrogenolysis afforded the most active A-diastereomer of the natural antibiotic TAN-1057 in 52% yield (from (S)-1 and 20a). Similarly, starting from (S)-1, a single diastereomer of the potent, less toxic TAN-1057A analogue 22b with a beta-lysine side chain has been prepared. All described synthetic steps do not require column chromatography for purification of the products. (C) 2004 Elsevier Ltd. All rights reserved.
• Reaction of S-methiodide derivatives of activated thioureas with hydroxylic compounds. Novel synthesis of mercaptans
  作者：Daniel L. Klayman、Robert J. Shine、J. David Bower

  DOI：10.1021/jo00975a015

  日期：1972.5
• Total Synthesis of TAN-1057 A/B, a New Dipeptide Antibiotic fromFlexibacter sp. PK-74
  作者：Viktor V. Sokolov、Sergei I. Kozhushkov、Sofia Nikolskaya、Vladimir N. Belov、Mazen Es-Sayed、Armin de Meijere

  DOI：10.1002/(sici)1099-0690(199805)1998:5<777::aid-ejoc777>3.0.co;2-w

  日期：1998.5

  23 (30%). The latter was deprotected by hydrogenolysis to give the final compound as a mixture of two epimers − TAN-1057A, B − isolated previously from a strain of Flexibacter sp. PK-74. The intermediate 3 was prepared from 3-amino-2-(N-Z-N-methylamino)propionic acid methyl ester hydrochloride (16) and 2-methyl-2-thiopseudobiuret hydroiodide (18) in one step in 35% yield.

  TAN-1057 (1a, b) - 一种对耐甲氧西林金黄色葡萄球菌具有活性的新型天然二肽抗生素 - 从 Nα、Nδ、Nω-tri-ZL-精氨酸 20b 开始，通过相应的重氮酮 21b 合成。这在光解后重排为烯酮，其被 (±)-2,4,5,6-四氢-5-甲氨基-2-脲基嘧啶-4-一 (3) 捕获，得到完全保护的二肽 23 (30%) . 后者通过氢解脱保护得到最终化合物，为两种差向异构体的混合物 - TAN-1057A，B - 先前从 Flexibacter sp. 菌株中分离。PK-74。中间体3由3-氨基-2-(NZN-甲基氨基)丙酸甲酯盐酸盐(16)和2-甲基-2-硫代伪缩二脲氢碘化物(18)一步制备，产率为35％。