188016-53-7

Usage

Uses

Used in Pharmaceutical and Biotechnology Industries:
N-BUTYLOXYCARBONYL-DAP-OH is used as a protective group in peptide synthesis for the amine functional group. Its role is crucial in the production of complex peptides, ensuring that the amine group remains protected during the synthesis process. The BOC group can be easily removed under mild conditions, enabling further functionalization of the amine for the development of pharmaceutical compounds and biotechnological applications.
Used in Peptide Synthesis:
N-BUTYLOXYCARBONYL-DAP-OH is used as a temporary protecting agent for the amine functional group during the synthesis of peptides. This protection allows chemists to carry out various reactions without affecting the amine group, which can be crucial for the peptide's biological activity. Once the desired modifications are complete, the BOC group can be removed, revealing the free amine group for further use or functionalization.

Upstream product

• 592-34-7 carbonochloridic acid, butyl ester 
• 188016-52-6 N-_α-n-butyloxycarbonyl-L-asparagine 

Downstream Products

• 188016-51-5 (2S)-2-butoxycarbonylamino-3-[2-[(5R)-3-(4-cyano-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetylamino]-propionic acid methyl ester 

Relevant academic research and scientific papers

The enantiospecific synthesis of an isoxazoline. A RGD mimic platelet GPIIb/IIIa antagonist

A convergent, large-scale, chiral synthesis of isoxazoline 1 has been achieved in 37% overall yield and > 99.6% optical purity, starting from L-asparagine and 4-cyanobenzaldehyde. Hofmann reaction of N(α)-n-Boc-L-asparagine with iodosobenzene diacetate provides optically pure N(α)-n-Boc-L-α,β-diaminopropionic acid (8) in 75% yield. A process of lipase resolution-base catalyzed epimerization gives the single enantiomer 5. Reaction of acid 5 with amine 9 in the presence of thionyl chloride forms the framework of 1. A Pinner reaction of intermediate 4 in methyl acetate or anisole, followed by an amidination with ammonium acetate, gives optically pure product 1.

Rearrangement of Nα-Protected L-Asparagines with Iodosobenzene Diacetate. A Practical Route to β-Amino-L-alanine Derivatives

A general synthetic method for the Hofmann rearrangement of protected asparagines has been developed. Reaction of asparagine derivatives with iodosobenzene diacetate (PIDA) in mixed solvents produces β-amino-L-alanines in good yield. Advantages over the commonly used reagent bis(trifluoroacetoxy)iodobenzene have been discussed.