Boc-L-Alanine Methyl Ester CASNO:28875-17-4

Chemical Identification

CAS Number: 28875-17-4

Molecular Formula: C9H17NO4

Molecular Weight: 203.24 g/mol

MDL Number: MFCD00038513

PubChem ID: 545713

SMILES: CC(C(=O)OC)NC(=O)OC(C)(C)C

Synonyms

Boc-L-Ala-OMe

N-(tert-Butoxycarbonyl)-L-alanine methyl ester

(S)-Methyl 2-(tert-butoxycarbonylamino)propanoate

Methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate

N-Boc-L-alanine methyl ester

Boc-L-Alanine Methyl Ester (CAS Number: 28875-17-4) is a protected amino acid derivative commonly used in peptide synthesis and organic chemistry. It features a tert-butoxycarbonyl (Boc) group protecting the amine and a methyl ester protecting the carboxyl group of L-alanine.

Physical and Chemical Properties

Appearance: White to off-white powder or low-melting solid

Melting Point: 32 – 35 °C (lit.)

Density: 1.03 g/mL at 25 °C

Optical Rotation:

Solubility: Soluble in methanol and common organic solvents

Storage Conditions: Refrigerated (0−8∘C), sealed, and stored under inert gas

 

Uses and Applications

Boc-L-Alanine Methyl Ester is widely used in chemical biology research, custom peptide synthesis, and pharmaceutical development.

  • Peptide Synthesis: Acts as a key building block (amino acid derivative) that protects the L-alanine moiety during the assembly of chirally-pure peptide sequences.
  • Pharmaceutical Intermediates: Utilized in the synthesis of peptidomimetic inhibitors (e.g., cytomegalovirus protease inhibitors) and various bioactive compounds.
  • Bioconjugation: Acts as a linker or intermediate in the synthesis of prodrugs and bioconjugates, including Hepatitis C virus inhibitor intermediates.
  • Research in Neuroscience: Used in the synthesis of neurotransmitter analogs.
  • Material Science: Employed in the creation of specialized polymers and hydrogels for biomedical applications (e.g., drug delivery).
  • Stereoselective Reactions: Can serve as a ligand in chemical reactions, displaying stereoselective properties.

Reactivity

The Boc group allows for selective, mild deprotection, making it compatible with various coupling reagents used in organic synthesis. It is relatively stable under normal conditions but should be kept away from strong oxidizing agents.

 

 

What is Boc-L-Alanine Methyl Ester?
Boc-L-Alanine Methyl Ester is a derivative of L-alanine where the amino group is protected by a tert-butoxycarbonyl (Boc) group and the carboxyl group is converted into a methyl ester.
What is the CAS number of Boc-L-Alanine Methyl Ester?

The CAS number is 28875-17-4.

What is the CAS number of Boc-L-Alanine Methyl Ester?

The CAS number is 28875-17-4.

What are the primary applications of this compound?

It is widely used in peptide synthesis, pharmaceutical intermediates, and organic synthesis.

Why is the Boc group used in this compound?

The Boc group protects the amino group during chemical reactions, preventing side reactions and enabling selective synthesis.

What is the function of the methyl ester group?

The methyl ester protects the carboxyl group and allows controlled deprotection in later synthesis steps.

FAQs

What is Boc-L-Alanine Methyl Ester?
Boc-L-Alanine Methyl Ester is a derivative of L-alanine where the amino group is protected by a tert-butoxycarbonyl (Boc) group and the carboxyl group is converted into a methyl ester.
What is the CAS number of Boc-L-Alanine Methyl Ester?

The CAS number is 28875-17-4.

What is the CAS number of Boc-L-Alanine Methyl Ester?

The CAS number is 28875-17-4.

What are the primary applications of this compound?

It is widely used in peptide synthesis, pharmaceutical intermediates, and organic synthesis.

Why is the Boc group used in this compound?

The Boc group protects the amino group during chemical reactions, preventing side reactions and enabling selective synthesis.

What is the function of the methyl ester group?

The methyl ester protects the carboxyl group and allows controlled deprotection in later synthesis steps.