N-[叔丁氧羰基]-N-甲基-O-苄基-D-酪氨酸 | 138774-98-8

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 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: N-[叔丁氧羰基]-N-甲基-O-苄基-D-酪氨酸
• 中文别名: BOC-N-甲基-O-苄基-D-酪氨酸
• 英文名称: Boc-D-MeTyr(Bzl)-OH
• 英文别名: (2R)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-(4-phenylmethoxyphenyl)propanoic acid
• CAS: 138774-98-8
• 化学式: C₂₂H₂₇NO₅
• 分子量: 385.46
• InChiKey: FSNRGORPOYPIJC-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2924299090
• 危险类别：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  N-[叔丁氧羰基]-N-甲基-O-苄基-D-酪氨酸 在 N-溴代丁二酰亚胺(NBS) 、 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 methyl (2R)-3-(3-bromo-4-phenylmethoxyphenyl)-2-[methyl-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoate
  参考文献：
  名称：

  Total synthesis and cytotoxicity of bisebromoamide and its analogues

  摘要：

  A highly convergent route for assembling bisebromoamide, its stereoisomers and a simplified analogue has been accomplished, which features connecting its left part and right part via thiazoline ring formation at the final stage. Preliminary biological studies revealed that compounds with both proposed and revised structures, and a simplified analogue have similar potency against the proliferation of HeLa S-3 cell, indicating that the stereochemistry of methylthiazoline part, and methyl group at the 4-methylproline residue in bisebromoamide, have limited influence on its cytotoxicity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.058
• 作为产物：
  描述：

  Boc-D-Tyr(Bzl)-OH 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 N-[叔丁氧羰基]-N-甲基-O-苄基-D-酪氨酸
  参考文献：
  名称：

  Alternative Synthesis of the Cycloisodityrosine Subunit of Deoxybouvardin, RA-VII, and Related Agents:  Reassignment of the Stereochemistry of Prior Intermediates

  摘要：

  DOI：

  10.1021/jo9604144

文献信息

• Synthesis of (9<i>R</i>,12<i>S</i>)- and (9<i>S</i>,12<i>S</i>)-Cycloisodityrosine and Their <i>N</i>-Methyl Derivatives
  作者：Dale L. Boger、Jiacheng Zhou、Robert M. Borzilleri、Seiji Nukui、Steven L. Castle

  DOI：10.1021/jo961346o

  日期：1997.4.1

  Full details of the synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives are detailed based on an intramolecular nucleophilic aromatic substitution reaction for formation of the key biaryl ether with 14-membered ring macrocyclization. Their comparison with prior samples and the documentation of a facile C9 epimerization within the natural 9S series are described.

  基于分子内亲核芳族取代反应以形成具有14元环大环化的关键联芳基醚，详细描述了（9R，12S）-和（9S，12S）-环异酪氨酸及其N-甲基衍生物的合成的详细信息。描述了它们与先前样品的比较以及天然9S系列中C9差向异构酶的简便记录。
• Total synthesis of natural (−)- and unnatural (+)-Melearoride A
  作者：Carson W. Reed、Mark G. Fulton、Kellie D. Nance、Craig W. Lindsley

  DOI：10.1016/j.tetlet.2019.02.006

  日期：2019.3

  This communication details the first total synthesis of the 13-membered macrolide, (−)-Melearoride A, as well as unnatural (+)-Melearoride A. The synthesis features a concise 13 step synthesis (11 steps longest linear sequence) that offers flexible stereo-control and multiple opportunities for unnatural analog synthesis to delve into antifungal SAR. The route features a cuprate addition, an Evans asymmetric

  本交流详细介绍了13元大环内酯类化合物（-）-美洛瑞A以及不自然的（+）-美洛瑞A的首次全合成。该合成具有简洁的13步合成法（最长11步线性序列），可提供灵活的立体控制以及非自然模拟合成深入研究抗真菌SAR的机会。这条路线的特点是添加了铜酸盐，埃文斯不对称烷基化和闭环易位（RCM），以关闭13元大环核心。
• Total synthesis and cytotoxicity of bisebromoamide and its analogues
  作者：Wenhua Li、Shouyun Yu、Mingzhi Jin、Hongguang Xia、Dawei Ma

  DOI：10.1016/j.tetlet.2010.11.058

  日期：2011.4

  A highly convergent route for assembling bisebromoamide, its stereoisomers and a simplified analogue has been accomplished, which features connecting its left part and right part via thiazoline ring formation at the final stage. Preliminary biological studies revealed that compounds with both proposed and revised structures, and a simplified analogue have similar potency against the proliferation of HeLa S-3 cell, indicating that the stereochemistry of methylthiazoline part, and methyl group at the 4-methylproline residue in bisebromoamide, have limited influence on its cytotoxicity. (C) 2010 Elsevier Ltd. All rights reserved.
• Alternative Synthesis of the Cycloisodityrosine Subunit of Deoxybouvardin, RA-VII, and Related Agents:  Reassignment of the Stereochemistry of Prior Intermediates
  作者：Dale L. Boger、Jiacheng Zhou

  DOI：10.1021/jo9604144

  日期：1996.1.1