(2R)-3-[(3-chlorophenyl)methoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid | 498576-54-8

• 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: (2R)-3-[(3-chlorophenyl)methoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 498576-54-8
• 化学式: C₁₅H₂₀ClNO₅
• 分子量: 329.781
• InChiKey: VNFHIIADODWEKY-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R)-3-[(3-chlorophenyl)methoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以88%的产率得到
  参考文献：
  名称：

  Synthesis of Photophore and Fluorophore Modified O-Benzylserine Derivatives

  摘要：

  O-Benzylation of serine is one of the important protection methods for solid phase peptide synthesis. The utilities of the protection group may be indicated that chemical modifications for O-benzylserine will be utilized to make functional peptides on solid phase synthesis. Detailed studies for effective synthesis of photoreactive and fluorophore containing O-benzylserine derivatives without racemization were reported.

  DOI：

  10.3987/com-16-s(s)37
• 作为产物：
  描述：

  BOC-D-丝氨酸 、 3-氯苄溴 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.25h， 以91%的产率得到(2R)-3-[(3-chlorophenyl)methoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
  参考文献：
  名称：

  Synthesis of Photophore and Fluorophore Modified O-Benzylserine Derivatives

  摘要：

  O-Benzylation of serine is one of the important protection methods for solid phase peptide synthesis. The utilities of the protection group may be indicated that chemical modifications for O-benzylserine will be utilized to make functional peptides on solid phase synthesis. Detailed studies for effective synthesis of photoreactive and fluorophore containing O-benzylserine derivatives without racemization were reported.

  DOI：

  10.3987/com-16-s(s)37

文献信息

• Design and synthesis of tetrazole-based growth hormone secretagogue: The SAR studies of the O-benzyl serine side chain
  作者：Jun Li、Stephanie Y. Chen、Shiwei Tao、Haixia Wang、James J. Li、Steve Swartz、Christa Musial、Andres A. Hernandez、Neil Flynn、Brian J. Murphy、Blake Beehler、Kenneth E. Dickinson、Leah Giupponi、Gary Grover、Ramakrishna Seethala、Paul Sleph、Dorothy Slusarchyk、Mujing Yan、William G. Humphreys、Hongjian Zhang、William R. Ewing、Jeffrey A. Robl、David Gordon、Joseph A. Tino

  DOI：10.1016/j.bmcl.2008.02.021

  日期：2008.3

  The structure-activity relationship of the O-benzyl serine side chain was investigated based on the tetrazole-based growth hormone secretagogue BMS-317180 (2). The ortho position of the benzyl moiety was found to be favorable for introduction of substituents. A series of ortho-substituted compounds were synthesized with improved in-vitro and in-vivo activity. Among them, the biphenyl compound 2p shows twofold improvement in potency compared to its parent compound BMS- 317180 (2). (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of Photophore and Fluorophore Modified O-Benzylserine Derivatives
  作者：Makoto Hashimoto、Takuma Yoshida、Zetryana Puteri Tachrim、Yasuko Sakihama、Yasuyuki Hashidoko、Yasumaru Hatanaka、Yuichi Kanaoka

  DOI：10.3987/com-16-s(s)37

  日期：——

  O-Benzylation of serine is one of the important protection methods for solid phase peptide synthesis. The utilities of the protection group may be indicated that chemical modifications for O-benzylserine will be utilized to make functional peptides on solid phase synthesis. Detailed studies for effective synthesis of photoreactive and fluorophore containing O-benzylserine derivatives without racemization were reported.