N-tert-butoxycarbonyl-L-methionine benzyl ester | 87746-57-4

• 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: N-tert-butoxycarbonyl-L-methionine benzyl ester
• 英文别名: Boc-Met-OBn；benzyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-methylsulfanylbutanoate
• CAS: 87746-57-4
• 化学式: C₁₇H₂₅NO₄S
• 分子量: 339.456
• InChiKey: BCKJGHFFUBJJJY-AWEZNQCLSA-N

物化性质

• 沸点：
  476.2±45.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  N-tert-butoxycarbonyl-L-methionine benzyl ester 在 bismuth(III) chloride 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以91%的产率得到Met-OBzl
  参考文献：
  名称：

  Chemoselective deprotection of N-Boc group in amino acids and peptides by bismuth(III) trichloride

  摘要：

  Selective deprotection of N-Boc group was achieved in excellent yields using bismuth(111) trichloride in a mixed solvent of acetonitrile and water (50: 1, v/v) at 55 degrees C. Acid-labile groups such as Pine and tert-butyl ester were not affected and no alkylation of tryptophan, methionine, and cysteine residues was observed under the deprotection conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.003
• 作为产物：
  描述：

  L-蛋氨酸 在 叔丁基亚氨基-三(二甲氨基)正膦 作用下， 以 乙腈 为溶剂， 反应 22.0h， 生成 N-tert-butoxycarbonyl-L-methionine benzyl ester
  参考文献：
  名称：

  Soluble α-Amino Acid Salts in Acetonitrile:  Practical Technology for the Production of Some Dipeptides

  摘要：

  [GRAPHICS]alpha-Amino acids are soluble in acetonitrile when treated with phosphazene bases. As a result, the protection/deprotection events that are usually required for peptide coupling reactions can be minimized. This is illustrated in the synthesis of the important angiotensin-converting enzyme (ACE) inhibitor enalapril.

  DOI：

  10.1021/ol020136x

文献信息

• Solventless Mechanosynthesis of N-Protected Amino Esters
  作者：Laure Konnert、Frédéric Lamaty、Jean Martinez、Evelina Colacino

  DOI：10.1021/jo500463y

  日期：2014.5.2

  planetary ball mill proved to be more suitable for the synthesis of amino esters from N-protected amino acids via a one-pot activation/esterification reaction in the presence of various dialkyl dicarbonates or chloroformates. The spot-to-spot reactions were straightforward, leading to the final products in reduced reaction times with improved yields and simplified work-up procedures.

  N-或C-保护的氨基酸的机械化学衍生化是在无溶剂条件下在球磨机中进行的。用于制备甲振动球磨机ñ -保护的α-和β-氨基酯从相应的起始N-通过在二-的存在下，氨基甲酰反应未掩蔽的前体叔丁基酯（BOC 2 O），氯甲酸苄酯（Z-Cl）或9-芴基甲氧基羰基氯甲酸酯（Fmoc-Cl）。事实证明，行星式球磨机更适合通过一锅法从N保护的氨基酸合成氨基酯各种二碳酸二烷基酯或氯甲酸酯存在下的活化/酯化反应。点对点反应简单明了，从而缩短了反应时间，提高了收率，简化了后处理程序，从而使最终产品成为可能。
• Synthesis of 2'-epi-distichonic acid A, an iron-chelating amino acid derivative.
  作者：TAKASHI TASHIRO、SHINJI FUSHIYA、SHIGEO NOZOE

  DOI：10.1248/cpb.36.893

  日期：——

  2'-epi-Distichonic acid A (4b), an iron-chelating amino acid derivative was synthesized starting from L-vinylglycine epoxide (6b). Reaction of 6b with glycine ester 17 afforded a β-hydroxy amino acid derivative (18). Reductive coupling of 21 derived from 18 with L-malic-β-semialdehyde (25) gave 2'-epi-distichonic acid A (4b) after deprotection.

  从L-乙烯基甘氨酸环氧化物（6b）出发，合成了一种铁螯合氨基酸衍生物2'-表双歧酸A（4b）。6b与甘氨酸酯17反应得到β-羟基氨基酸衍生物（18）。由18衍生的21与L-苹果酸-β-半醛（25）进行还原偶联，去保护后得到2'-表双歧酸A（4b）。
• Asymmetric Intermolecular Conjugate Addition of Amino Acid Derivatives via Memory of Chirality: Total Synthesis of Manzacidin A
  作者：Tomoyuki Yoshimura、Tomohiko Kinoshita、Hiroyasu Yoshioka、Takeo Kawabata

  DOI：10.1021/ol303568f

  日期：2013.2.15

  Asymmetric intermolecular conjugate addition of α-amino acid derivatives with 4 via memory of chirality has been developed. The reactions proceeded in up to 98% ee with retention of configuration at the newly formed tetrasubstituted carbon center when R = Me. The product (R = Me) was transformed into manzacidin A.

  已经开发了通过手性记忆的α-氨基酸衍生物与4的不对称分子间共轭加成。当R = Me时，反应以高达98％ee的温度进行，并保留了新形成的四取代碳中心的构型。产物（R = Me）被转化为甘露糖苷A。
• DEPROTECTION METHOD
  申请人：AJINOMOTO CO., INC.

  公开号：US20160024143A1

  公开（公告）日：2016-01-28

  The present invention provides a method of efficiently deprotecting a protected organic compound by catalytic hydrogenation. Specifically, the present invention provides a method of deprotecting an organic compound having at least one functional group selected from the group consisting of a carboxy group, an amino group and a hydroxy group, which is protected by a protecting group represented by the formula (I): R 1 —C(R 2 )(R 3 )-L 1 -   (I) [wherein R 1 is an aryl group optionally having substituent(s), R 2 and R 3 are each independently, a hydrogen atom or an aryl group optionally having substituent(s), and L 1 is a single bond, —O—CO— or —O—CH 2 —], comprising hydrogenation in the presence of a metal catalyst and halogenated acetic acid.

  本发明提供了一种通过催化氢化高效去保护有机化合物的方法。具体而言，本发明提供了一种去保护具有至少一种来自羧基、氨基和羟基的官能团的有机化合物的方法，该官能团由式(I)所表示的保护基所保护，该式中R1为一个芳基，可选地具有取代基，R2和R3分别独立地为氢原子或可选地具有取代基的芳基，L1为单键，-O-CO-或-O-CH2-，包括在金属催化剂和卤代乙酸存在下进行氢化的步骤。