tert-butyl 2-[(tert-butoxycarbonyl)amino]-3,3,4,4-tetradeutero-4-(tritylsulfanyl)-butanoate | 298195-47-8

• 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: tert-butyl 2-[(tert-butoxycarbonyl)amino]-3,3,4,4-tetradeutero-4-(tritylsulfanyl)-butanoate
• 英文别名: Tert-butyl 3,3,4,4-tetradeuterio-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-tritylsulfanylbutanoate
• CAS: 298195-47-8
• 化学式: C₃₂H₃₉NO₄S
• 分子量: 537.7
• InChiKey: MTOYOBJZQLNZQS-ORRLFXPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[(tert-butoxycarbonyl)amino]-3,3,4,4-tetradeutero-4-(tritylsulfanyl)-butanoate 在 碘 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.75h， 以87%的产率得到di(tert-butyl) 2,2,17,17-tetramethyl-4,15-dioxo-7,7,8,8,11,11,12,12-octadeutero-3,16-dioxa-9,10-dithia-5,14-diazaoctadecane-6,13-dicarboxylate
  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：

  三苯甲硫醇 在 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 环己烷 为溶剂， 反应 4.75h， 生成 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

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.