N-t-Boc-valacyclovir

CAS: 502421-44-5

Ref. 3D-FB18986

Product Information

• Name: N-t-Boc-valacyclovir
• Synonyms: N-tert-Butoxycarbonyl-L-valine-2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester, (S)-2-((2-Imino-6-oxo-2,3-dihydro-1H-purin-9(6H)-yl)methoxy)ethyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate, 2-[(2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl N-(tert-butoxycarbonyl)-L-valinate, <span class="text-smallcaps">L</span>-Valine, N-[(1,1-dimethylethoxy)carbonyl]-, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester, L-valine, N-[(1,1-dimethylethoxy)carbonyl]-, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester, N-[(1,1-Dimethylethoxy)carbonyl]-<span class="text-smallcaps">L</span>-valine 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester

Description

Valacyclovir is a prodrug that is hydrolyzed to acyclovir in the body. Valacyclovir is an ester of valine and cyclovir. The synthesis starts with the coupling of N-t-Boc-valine to 2,4-dichlorobenzyl alcohol. The product is then subjected to hydrolysis with hydrochloric acid in refluxing isopropanol, which yields N-t-Boc-valacyclovir. Hydrolysis of this compound under basic conditions gives the desired acyclovir. Acetylation of the hydroxyl group on the side chain of valine forms a methyl ester, which can be cleaved using an acidic solution (e.g., HCl) to give valacyclovir.

• Brand: Biosynth

Chemical properties

• Molecular weight: 424.45 g/mol
• Formula: C₁₈H₂₈N₆O₆
• Purity: Min. 95%
• Color/Form: Powder