(S)-3-(4-Boronophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid

Name: (S)-3-(4-Boronophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid
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CAS No. 119771-23-2
Cat. No. CS-0059703
Purity≥97%
MDL No.None

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(S)-3-(4-Boronophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid|CS-0059703

Structure of 119771-23-2

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General Information

CAS No. 119771-23-2
Cat. No. CS-0059703
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₀BNO₆
Molecular Weight 309.12
Synonym(s) (S)-3-(4-boronophenyl)-2-((tert-butoxycarbonyl)amino)propanoicacid
SMILES C([C@@H](NC(=O)OC(C)(C)C)CC=1C=CC(=CC1)B(O)O)(=O)O

Description

(S)-3-(4-Boronophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid features a boronate group enabling efficient Suzuki-Miyaura coupling, paired with a stable tert-butyl carbamate-protected amine. This configuration supports modular peptide and heterocyclic scaffold synthesis under standard conditions.

Application

(S)-3-(4-Boronophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid serves as a versatile building block for the synthesis of boron-containing amino acids and peptidomimetics. The pendant boronate ester enables facile Suzuki-Miyaura coupling, while the Boc-protected amine and carboxylic acid functionalities offer orthogonal reactivity for peptide elongation and conjugation. Its bench-stable nature and compatibility with standard purification methods make it well-suited for iterative synthetic workflows in medicinal chemistry and target-oriented synthesis.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  76410-58-7
- ~%
- In-stock
  
  119771-23-2
References
- Bednarz, Mark S.; Burgoon, JR., Hugh Alfred; Iimura, Shinya; Kanamarlapudi, Ramanaiah C.; Song, Qiuling; Wu, Wenxue; Yan, Jie; Zhang, Haiming Patent: US2009/62540 A1, 2009 ; Location in patent: Page/Page column 9 ;
Route2
- 262604-04-6
- ~%
- In-stock
  
  119771-23-2
References
- Nakamura, Hiroyuki; Fujiwara, Masaru; Yamamoto, Yoshinori Bulletin of the Chemical Society of Japan, 2000 , vol. 73, # 1 p. 231 - 235

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 116.09
LogP -0.1132
H_Acceptors 5
H_Donors 4
Rotatable_Bonds 5

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-3-(4-Boronophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid

CAS No. 119771-23-2

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