1,1,2,2-tetradeutero-2-bromoethyl triphenylmethyl sulfide

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1,1,2,2-tetradeutero-2-bromoethyl triphenylmethyl sulfide
• 英文别名: [(2-Bromo-1,1,2,2-tetradeuterioethyl)sulfanyl-diphenylmethyl]benzene
• 化学式: C₂₁H₁₉BrS
• 分子量: 387.32
• InChiKey: LTIKGYXXFFGAEY-RZOBCMOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Boc-甘氨酸叔-丁基酯 、 1,1,2,2-tetradeutero-2-bromoethyl triphenylmethyl sulfide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 0.5h， 以24%的产率得到tert-butyl 2-[(tert-butoxycarbonyl)amino]-3,3,4,4-tetradeutero-4-(tritylsulfanyl)-butanoate
  参考文献：
  名称：

  A facile synthesis of 3,3,4,4,3′,3′,4′,4′-homocystine-d8

  摘要：

  We describe the synthesis of 3,3,4,4,3',3',4',4'-homocystine-d(8) 2 in four steps. Compound 2 has been utilized as an internal standard for the LC-MS quantification of L-homocysteine 1, a marker for cardiac disease. 1,1,2,2-Tetradeutero-2-bromoethyl triphenylmethyl sulfide 4 was treated with the dianion of N-(tert-butoxycarbonyl) glycine tert-butyl ester 5 giving the homocysteine derivative 6. Oxidation of 6 with iodine in methanol gave the homocystine precursor 7. Subsequent deprotection provided 2 in high chemical purity (99%) as measured by analytical HPLC and isotopic purity of >99% as determined by mass spectrometry.

  DOI：

  10.1002/1099-1344(200008)43:9<909::aid-jlcr376>3.0.co;2-9
• 作为产物：
  描述：

  1,2-二溴乙烷-D4 、 三苯甲硫醇 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.25h， 以98%的产率得到1,1,2,2-tetradeutero-2-bromoethyl triphenylmethyl sulfide
  参考文献：
  名称：

  A facile synthesis of 3,3,4,4,3′,3′,4′,4′-homocystine-d8

  摘要：

  We describe the synthesis of 3,3,4,4,3',3',4',4'-homocystine-d(8) 2 in four steps. Compound 2 has been utilized as an internal standard for the LC-MS quantification of L-homocysteine 1, a marker for cardiac disease. 1,1,2,2-Tetradeutero-2-bromoethyl triphenylmethyl sulfide 4 was treated with the dianion of N-(tert-butoxycarbonyl) glycine tert-butyl ester 5 giving the homocysteine derivative 6. Oxidation of 6 with iodine in methanol gave the homocystine precursor 7. Subsequent deprotection provided 2 in high chemical purity (99%) as measured by analytical HPLC and isotopic purity of >99% as determined by mass spectrometry.

  DOI：

  10.1002/1099-1344(200008)43:9<909::aid-jlcr376>3.0.co;2-9

文献信息

• A facile synthesis of 3,3,4,4,3′,3′,4′,4′-homocystine-d8
  作者：Maciej Adamczyk、Jeffrey R. Fishpaugh、Mohan Thiruvazhi

  DOI：10.1002/1099-1344(200008)43:9<909::aid-jlcr376>3.0.co;2-9

  日期：2000.8

  We describe the synthesis of 3,3,4,4,3',3',4',4'-homocystine-d(8) 2 in four steps. Compound 2 has been utilized as an internal standard for the LC-MS quantification of L-homocysteine 1, a marker for cardiac disease. 1,1,2,2-Tetradeutero-2-bromoethyl triphenylmethyl sulfide 4 was treated with the dianion of N-(tert-butoxycarbonyl) glycine tert-butyl ester 5 giving the homocysteine derivative 6. Oxidation of 6 with iodine in methanol gave the homocystine precursor 7. Subsequent deprotection provided 2 in high chemical purity (99%) as measured by analytical HPLC and isotopic purity of >99% as determined by mass spectrometry.