N²-benzyloxycarbonyl-N²-methyl-L-asparagine | 475296-58-3

• 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: N²-benzyloxycarbonyl-N²-methyl-L-asparagine
• 英文别名: N-benzyloxycarbonyl-N-methyl-L-asparagine；N²-Z-N²-Me-L-AsnOH；(2S)-4-amino-2-[methyl(phenylmethoxycarbonyl)amino]-4-oxobutanoic acid
• CAS: 475296-58-3
• 化学式: C₁₃H₁₆N₂O₅
• mdl: MFCD01058369
• 分子量: 280.28
• InChiKey: WYDIYVSIFPKQFO-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N²-benzyloxycarbonyl-N²-methyl-L-asparagine 在 sodium hydroxide 、 sodium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 23.5h， 生成 (S)-2-(N-benzyloxycarbonyl-N-methyl)amino-3-(tert-butoxycarbonylamino)propionic acid
  参考文献：
  名称：

  First enantioselective synthesis of the novel antiinfective TAN-1057A via its aminomethyl-substituted dihydropyrimidinone heterocycle

  摘要：

  Enantiomerically pure N-2-Z-N-2-MeAsnOH [(S)-14], prepared in 8 steps (23% overall yield) from asparaginic acid, was first subjected to a Hofmann degradation with PhI(OCOCF3)(2) yielding (S)-N-2-Z-N-2-methyl-2,3-diaminopropanoic acid [N-2-Z-N-2-Me-L-A(2)pr, (S)-15], and this in turn was protected to give N-2-Z-N-3-Boc-N-2-Me-L-A(2)pr [(S)-17]. Condensation of (S)-17 with HN=C(SMe)NHCONH2 followed by removal of the tert-butoxycarbonyl protecting group, cyclization and hydrogenolytic removal of the Z-group gave the heterocycle of TAN-1057A [(S)-1] with an e.e. of 87 in 36% yield [from (S)-14]. Coupling of (S)-1 with (S)-tris-Z-beta-homoarginine (20a) in the presence of O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) and iPr(2)NEt in N,N-dimethyl-acetamide followed by hydrogenolysis afforded the most active A-diastereomer of the natural antibiotic TAN-1057 in 52% yield (from (S)-1 and 20a). Similarly, starting from (S)-1, a single diastereomer of the potent, less toxic TAN-1057A analogue 22b with a beta-lysine side chain has been prepared. All described synthetic steps do not require column chromatography for purification of the products. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.034
• 作为产物：
  描述：

  (S)-3-carbonylbenzyloxy-4-(triphenylmethylaminoacetoyl)-oxazolidin-5-one 在 三乙基硅烷 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以86%的产率得到N²-benzyloxycarbonyl-N²-methyl-L-asparagine
  参考文献：
  名称：

  N-甲基天冬酰胺，精氨酸，组氨酸和色氨酸的新型合成。

  摘要：

  [反应：见正文]肽中的N-甲基氨基酸残基修饰了几个药理上有用的参数，但由于N-甲基化单体的缺乏，烷基化肽的合成受到了阻碍。提出了具有碱性侧链的四个N-甲基氨基酸的合成。这些碱性氨基酸的侧链需要特别保护或构建。这完成了我们小组通过5-恶唑烷酮中间体制备的20种常见L-氨基酸N-甲基衍生物的集合。

  DOI：

  10.1021/ol026799w

文献信息

• [EN] N-METHYL AMINO ACIDS<br/>[FR] ACIDES N-METHYL AMINES
  申请人：UBIQUITOUS TECHNOLOGIES PTY LT

  公开号：WO2004007427A1

  公开（公告）日：2004-01-22

  The present invention relates to a compound of formula (I) or (II), processes for preparing them, peptides including them and kits involving them.

  这项发明涉及到式(I)或(II)的化合物，制备它们的方法，包括它们的肽和涉及它们的试剂盒。
• N-methyl amino acids
  申请人：Aurelio Luigi

  公开号：US20050245432A1

  公开（公告）日：2005-11-03

  The present invention relates to a compound of formula (I) or (II), processes for preparing them, peptides including them and kits involving them.

  本发明涉及公式(I)或(II)化合物，制备它们的方法，包括它们的肽和涉及它们的试剂盒。
• An Efficient Synthesis of <i>N</i>-Methyl Amino Acids by Way of Intermediate 5-Oxazolidinones
  作者：Luigi Aurelio、John S. Box、Robert T. C. Brownlee、Andrew B. Hughes、Marianne M. Sleebs

  DOI：10.1021/jo026722l

  日期：2003.4.1

  N-Methyl amino acids occur in many natural products. Experimental strategies are presented for a unified approach to the synthesis of N-methyl derivatives through 5-oxazolidinones of the 20 common L-amino acids. The amino acids with reactive side chains that required protecting groups or devoted syntheses for side chain construction for N-methylation to proceed included serine, threonine, tyrosine, cysteine, methionine, tryptophan, asparagine, histidine, and arginine. The studies have provided improved methods for the preparation of N-methyl serine, threonine, and tyrosine. All 20 of the common L-amino acids are now available in suitable forms for solid or solution-phase peptide synthesis.