(S)-3-((叔丁氧基羰基)氨基)-4-氟-4-氧代丁酸苄酯 | 133010-11-4

• 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
• 中文名称: (S)-3-((叔丁氧基羰基)氨基)-4-氟-4-氧代丁酸苄酯
• 英文名称: Boc-Asp(OBzl)-F
• 英文别名: BOC-Asp(OBn)-F；(S)-Benzyl 3-((tert-butoxycarbonyl)amino)-4-fluoro-4-oxobutanoate；benzyl (3S)-4-fluoro-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate
• CAS: 133010-11-4
• 化学式: C₁₆H₂₀FNO₅
• 分子量: 325.337
• InChiKey: JGAYWOLCVLNHQD-LBPRGKRZSA-N

物化性质

• 熔点：
  52-54 °C
• 沸点：
  465.7±45.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  (S)-3-((叔丁氧基羰基)氨基)-4-氟-4-氧代丁酸苄酯 、 (S)-1-((S)-2-Allylamino-6-benzyloxycarbonylamino-hexanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到Boc-Asp(OBn)-N(allyl)Lys(Cbz)-Pro-OtBu
  参考文献：
  名称：

  Triflates as synthons for the synthesis of lysine analogues

  摘要：

  A simple synthesis of various 6-amino-2-substituted hexanoic acids has been developed starting from lysine via the triflate of 6-amino-2-hydroxy hexanoic acid. The same reactions have also been successfully applied starting from the lysyl-proline sequence. The lysine analogues have been introduced in pseudopeptide sequences by the acylfluoride methodology. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01445-8
• 作为产物：
  描述：

  Boc-L-天冬氨酸 4-苄酯 在 吡啶 、 三聚氟氰 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以89%的产率得到(S)-3-((叔丁氧基羰基)氨基)-4-氟-4-氧代丁酸苄酯
  参考文献：
  名称：

  tert-Butyloxycarbonyl and benzyloxycarbonyl amino acid fluorides. New, stable rapid-acting acylating agents for peptide synthesis

  摘要：

  A new class of rapid-acting acylating agents, alpha-BOC and Z amino acid fluorides are obtained as stable, often crystalline, compounds by treatment of the protected amino acid with cyanuric fluoride.

  DOI：

  10.1021/jo00008a005

文献信息

• A Convenient, One-Pot Procedure for the Preparation of Acyl and Sulfonyl Fluorides Using Cl3CCN, Ph3P, and TBAF(t-BuOH)4
  作者：Doo Jang、Joong-Gon Kim

  DOI：10.1055/s-0030-1259051

  日期：2010.12

  Various carboxylic acids were converted into acyl fluorides in excellent yields by treatment with trichloroacetonitrile, triphenylphosphine, and TBAF(t-BuOH) 4 at room temperature. The reaction was applicable to the preparation of acid-sensitive amino acid fluorides without deprotection or rearrangement.

  通过在室温下用三氯乙腈、三苯基膦和 TBAF(t-BuOH) 4 处理，各种羧酸以优异的产率转化为酰氟。该反应可用于制备酸敏感的氨基酸氟化物，无需脱保护或重排。
• tert-Butyloxycarbonyl and benzyloxycarbonyl amino acid fluorides. New, stable rapid-acting acylating agents for peptide synthesis
  作者：Louis A. Carpino、El-Sayed M. E. Mansour、Dean Sadat-Aalaee

  DOI：10.1021/jo00008a005

  日期：1991.4

  A new class of rapid-acting acylating agents, alpha-BOC and Z amino acid fluorides are obtained as stable, often crystalline, compounds by treatment of the protected amino acid with cyanuric fluoride.
• Synthesis of 1,2,4-oxadiazole-linked orthogonally urethane-protected dipeptide mimetics
  作者：Vommina V. Sureshbabu、Hosahalli P. Hemantha、Shankar A. Naik

  DOI：10.1016/j.tetlet.2008.06.091

  日期：2008.8

  The synthesis of a new class of 1,2,4-oxadiazole-linked orthogonally urethane-protected dipeptide mimetics is described. The protocol employs a reaction between an N-protected amino acyl fluoride and an amino acid-derived amidoxime. All the three commonly employed urethanes have been used in this protocol for N-protection. The course of the reaction was found to be high yielding and all new compounds were well characterized by NMR and mass spectroscopy. The C-acyl amidoxime intermediate has also been isolated as a stable solid. (C) 2008 Elsevier Ltd. All rights reserved.
• Protected .beta.- and .gamma.-aspartic and -glutamic acid fluorides
  作者：Louis A. Carpino、El Sayed M. E. Mansour

  DOI：10.1021/jo00049a065

  日期：1992.11
• CARPINO, LOUIS A.;MANSOUR, EL-SAYED M. E.;SADAT-AALAEE, DEAN, J. ORG. CHEM., 56,(1991) N, C. 2611-2614
  作者：CARPINO, LOUIS A.、MANSOUR, EL-SAYED M. E.、SADAT-AALAEE, DEAN

  DOI：——

  日期：——