((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid | 405096-74-4

• 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: ((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid
• CAS: 405096-74-4
• 化学式: C₁₆H₂₂N₂O₇S
• 分子量: 386.426
• InChiKey: XRPYEWXWYAYYHT-FZMZJTMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  138.87
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid 在 palladium on activated charcoal 草酰氯 、 氢气 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 [(4aS,7R,7aR)-4-carbamoyl-2-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyridin-7-yl] 2-[[(2S,3S)-2-amino-3-methylpentanoyl]sulfamoyl]acetate
  参考文献：
  名称：

  Synthesis and activity of analogues of the isoleucyl tRNA synthetase inhibitor SB-203207

  摘要：

  Twenty two analogues of SB-203207 have been prepared by total synthesis, and evaluated as inhibitors of a range of tRNA synthetases. Changes to the bicyclic core, removing either the terminal amino substituent or the sulfonyl group from the side chain, and altering either the carbon skeleton or stereochemistry of the isoleucine residue, decreases the potency of inhibition of isoleucyl tRNA synthetase. Substituting the isoleucine residue with other amino acids produces inhibitors of the corresponding synthetases. In particular, a methionine derivative is 50-100 times more potent against methionyl tRNA synthetase than against any of the corresponding isoleucyl, leucyl, valyl, alanyl and prolyl synthetases. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00237-2
• 作为产物：
  描述：

  ((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 ((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylsulfamoyl)-acetic acid
  参考文献：
  名称：

  Synthesis and activity of analogues of the isoleucyl tRNA synthetase inhibitor SB-203207

  摘要：

  Twenty two analogues of SB-203207 have been prepared by total synthesis, and evaluated as inhibitors of a range of tRNA synthetases. Changes to the bicyclic core, removing either the terminal amino substituent or the sulfonyl group from the side chain, and altering either the carbon skeleton or stereochemistry of the isoleucine residue, decreases the potency of inhibition of isoleucyl tRNA synthetase. Substituting the isoleucine residue with other amino acids produces inhibitors of the corresponding synthetases. In particular, a methionine derivative is 50-100 times more potent against methionyl tRNA synthetase than against any of the corresponding isoleucyl, leucyl, valyl, alanyl and prolyl synthetases. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00237-2

文献信息

• Enantioselective Synthesis of SB-203207
  作者：Yasuo Hirooka、Kazutada Ikeuchi、Yuichiro Kawamoto、Yusuke Akao、Takumi Furuta、Tomohiro Asakawa、Makoto Inai、Toshiyuki Wakimoto、Tohru Fukuyama、Toshiyuki Kan

  DOI：10.1021/ol5002973

  日期：2014.3.21

  Total synthesis of SB-203207 (1) was achieved, beginning with a desymmetrical C–H insertion reaction of a diazoester bearing our recently developed chiral auxiliary. Utilizing the optically active bicyclo[3.3.0]octane ring, four stereogenic centers were efficiently constructed in sequence. Finally, mild oxidation of 27 to carboxylic acid via a cyanohydrin intermediate and hydrolysis of cyanide to carboxyamide

  从带有我们最近开发的手性助剂的重氮酯的不对称CH插入反应开始，实现了SB-203207（1）的总合成。利用光学活性的双环[3.3.0]辛烷环，可以有效地依次构建四个立体异构中心。最后，在不稳定的烯酰胺基团的存在下，通过氰醇中间体将27轻度氧化为羧酸，然后将氰化物水解为羧酰胺，完成了1的有效全合成。
• ——
  作者：Martin G. Banwell、Curtis F. Crasto、Christopher J. Easton、Tomislav Karoli、Darren R. March、Michael R. Nairn、Peter J. O’Hanlon、Mark D. Oldham、Anthony C. Willis、Weimin Yue

  DOI：10.1039/b104890m

  日期：2001.10.23

  The ketone (+/-)- 5, which embodies the bicyclic core associated with the title tRNA synthetase inhibitors 1 and 2, has been prepared via a three-component coupling reaction involving 2-( hydroxymethyl) cyclopent-2-enone (15), methylamine (6) and propiolamide (10); straightforward elaboration of the readily derived acetates ()- 21 and (+)- 21 has provided the biologically active analogues 23 and 24, respectively, of the title compounds.