(S,S)-2,7-bis<<(benzyloxy)carbonyl>amino>octanedioic acid dimethyl ester | 73872-72-7

• 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: (S,S)-2,7-bis<<(benzyloxy)carbonyl>amino>octanedioic acid dimethyl ester
• 英文别名: (2S,7S)-2,7-bis(benzyloxycarbonylamino)octane-1,8-dioic acid dimethyl este；dimethyl (2S,7S)-2,7-bis(phenylmethoxycarbonylamino)octanedioate
• CAS: 73872-72-7
• 化学式: C₂₆H₃₂N₂O₈
• 分子量: 500.549
• InChiKey: JJLTWEOEZROGBJ-VXKWHMMOSA-N

物化性质

• 沸点：
  654.9±55.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S,S)-2,7-bis<<(benzyloxy)carbonyl>amino>octanedioic acid dimethyl ester 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 96.0h， 生成 (S,S)-2,7-bis<<(benzyloxy)carbonyl>amino>octanedioic acid bis(2-oxo-2-phenylethyl) ester
  参考文献：
  名称：

  Efficient Synthesis of Differentially Protected (S,S)-2,7- Diaminooctanedioic Acid, the Dicarba Analogue of Cystine

  摘要：

  Convenient preparative syntheses of differentially protected forms of (S,S)-2,7-diaminooctanedioic acid (2), suitable for application in peptide chemistry, are described. The key compound, the di-Cbz-protected phenacyl monoester 7a (Cbz = [(benzyloxy)carbonyl]), was obtained by means of Schollkopf bis-lactim ether methodology and optimized monoesterification procedures. Selective amino deprotection at the non-esterified amino-acid function of 7a by dichloromethyl-methyl-ether-induced 'N-carboxyanhydride' formation, and hydrolysis permitted access to the Boc/Cbz- and Fmoc/Cbz-protected monophenacyl esters 11a and 11b, as well as to the fully orthogonally protected Fmoc/Boc monophenacyl ester 12 (Boc = (teri-butoxy)carbonyl, Fmoc = (9H-fluoren-9-ylmethoxy)carbonyl).

  DOI：

  10.1002/(sici)1522-2675(19981111)81:11<2053::aid-hlca2053>3.0.co;2-4
• 作为产物：
  描述：

  Z-L-GluOMe 在 sodium methylate 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 8.0h， 以18%的产率得到(S,S)-2,7-bis<<(benzyloxy)carbonyl>amino>octanedioic acid dimethyl ester
  参考文献：
  名称：

  使用Kolbe电解法制备2,7-二氨基丁二酸和2,5-二氨基己二酸衍生物的详细研究

  摘要：

  通过N-保护的α-谷氨酸酯的Kolbe反应制备的被保护的2,7-二氨基硫酸（DAS）的产率取决于溶剂，温度，羧酸根阴离子的浓度和保护基团。以Boc-Glu-OMe为起始原料，以MeOH /吡啶/ NaOMe为电解质，得到最高的保护的L，L -2,7-二氨基丁二酸。

  DOI：

  10.1016/s0040-4020(97)10412-4

文献信息

• Enantioselective Synthesis of Diamino Dicarboxylic Acids
  作者：Johann Hiebl、Hermann Kollmann、Franz Rovenszky、Karin Winkler

  DOI：10.1021/jo982034j

  日期：1999.3.1

  The preparation of alkyl diamino dicarboxylic acids with high optical purity (100% ee, >98.5% de) and high yields based on asymmetric catalytic hydrogenation is described. The required prochiral precursors are prepared from dialdehydes and Z-, Boc-, and acetyl-protected phosphonoglycines. Aqueous solutions of glyoxal, succinic dialdehyde, and glutaric dialdehyde were used to prepare the diunsaturated

  描述了基于不对称催化氢化制备具有高光学纯度（100％ee，＞ 98.5％de）和高产率的烷基二氨基二羧酸。所需的前手性前体由二醛和Z-，Boc-和乙酰基保护的膦酰甘氨酸制备。使用乙二醛，琥珀酸二醛和戊二醛的水溶液制备2,5-二氨基己二酸（DAA），2,7-二氨基丁二酸（DAS）和2,8-二氨基壬二酸（DAZ）的双不饱和前体。通过用[（COD）Rh（S，S）-Et-DuPHOS] OTf氢化相应的前手性原料，获得ZA保护的DAA，DAS和DAZ二甲基酯。
• Optimization of the Linker Length in the Dimer Model of E22P-Aβ40 Tethered at Position 38
  作者：Ayaka Chikugo、Yumi Irie、Chihiro Tsukano、Ayumi Uchino、Takahito Maki、Toshiaki Kume、Taiji Kawase、Kenji Hirose、Yusuke Kageyama、Ikuo Tooyama、Kazuhiro Irie

  DOI：10.1021/acschemneuro.2c00436

  日期：2022.10.5
• A detailed investigation of the preparation of 2,7-diaminosuberic acid and 2,5-diaminoadipic acid derivatives using Kolbe electrolysis
  作者：Johann Hiebl、Michael Blanka、Andras Guttman、Hermann Kollmann、Kornelia Leitner、Günter Mayrhofer、Franz Rovenszky、Karin Winkler

  DOI：10.1016/s0040-4020(97)10412-4

  日期：1998.3

  The yield of protected 2,7- diaminosuberic acid (DAS) prepared by Kolbe reaction of N-protected α-glutamic acid esters is dependent on solvent, temperature, concentration of carboxylate anion, and protecting groups. The highest yield of protected L,L-2,7-diaminosuberic acid is obtained with Boc-Glu-OMe as starting material using MeOH/pyridine/NaOMe as electrolyte.

  通过N-保护的α-谷氨酸酯的Kolbe反应制备的被保护的2,7-二氨基硫酸（DAS）的产率取决于溶剂，温度，羧酸根阴离子的浓度和保护基团。以Boc-Glu-OMe为起始原料，以MeOH /吡啶/ NaOMe为电解质，得到最高的保护的L，L -2,7-二氨基丁二酸。
• Efficient Synthesis of Differentially Protected (S,S)-2,7- Diaminooctanedioic Acid, the Dicarba Analogue of Cystine
  作者：Meinolf Lange、Peter M. Fischer

  DOI：10.1002/(sici)1522-2675(19981111)81:11<2053::aid-hlca2053>3.0.co;2-4

  日期：1998.11.11

  Convenient preparative syntheses of differentially protected forms of (S,S)-2,7-diaminooctanedioic acid (2), suitable for application in peptide chemistry, are described. The key compound, the di-Cbz-protected phenacyl monoester 7a (Cbz = [(benzyloxy)carbonyl]), was obtained by means of Schollkopf bis-lactim ether methodology and optimized monoesterification procedures. Selective amino deprotection at the non-esterified amino-acid function of 7a by dichloromethyl-methyl-ether-induced 'N-carboxyanhydride' formation, and hydrolysis permitted access to the Boc/Cbz- and Fmoc/Cbz-protected monophenacyl esters 11a and 11b, as well as to the fully orthogonally protected Fmoc/Boc monophenacyl ester 12 (Boc = (teri-butoxy)carbonyl, Fmoc = (9H-fluoren-9-ylmethoxy)carbonyl).