13498-74-3

Upstream product

• 39149-80-9 tert-butyl 2-bromopropionate 
• 1149-26-4 N-benzyloxycarbonylvaline 
• 238399-55-8 4-methoxybenzyl (S)-(+)-2-(N-CBz-L-valyloxy)propionate 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 

Downstream Products

• 1328880-68-7 2',3'-dideoxy-3'-fluoro-5'-O-[(S)-(+)-2-(N-Cbz-L-valyloxy)-propionyl]guanosine 
• 13499-02-0 Z-L-Val-L-Lac-D-Val-D-HyIv 
• 13798-70-4 Z-L-Val-L-Lac-D-Val-D-HyIv-L-Val-L-Lac-D-Val-D-HyIv-OtBu 
• 13509-22-3 Z-L-Val-L-Lac-D-Val-D-HyIv-L-Val-L-Lac-D-Val-D-HyIv 
• 13498-82-3 Z-L-Val-L-Lac-D-Val-D-HyIv-OtBu 

Relevant academic research and scientific papers

N4-HYDROXYCYTIDINE AND DERIVATIVES AND ANTI-VIRAL USES RELATED THERETO

This disclosure relates to certain N4-hydroxycytidine derivatives, pharmaceutical compositions, and methods related thereto. In certain embodiments, the disclosure relates to the treatment or prophylaxis of human coronavirus 2019-nCoV.

Synthesis of the hepatitis B nucleoside analogue lagociclovir valactate

2′,3′-Dideoxy-3′-fluoro-5-O-[(S)-(+)-2-(l-valyloxy) -propionyl guanosine (lagociclovir valactate) is a prodrug of 3′-fluoro-2′,3′-dideoxyguanosine with high oral bioavailability in humans and potent activity against hepatitis B virus (HBV). A five-step synthesis of lagocyclovir valactate starting from 2-amino-6-chloropurine is described. The synthesis was performed at kilogram scale, and the target nucleoside prodrug was isolated as the hemisulphate salt with an overall yield of 23%. The major challenges were N-glycosylation of a 2-deoxyfluorosugar, which required separation of α- and β-anomers, and deprotection of the penultimate intermediate by hydrogenation.

Non-nucleoside reverse transcriptase inhibitors

Non-nucleoside reverse transcriptase inhibitors of formula (P-1) wherein: Ar1 is an unsaturated, optionally substituted, mono or bicyclic ring structure comprising 0 to 3 hetero atoms selected from S, O and N; Ar2 is an aromatic, optionally substituted, monocyclic ring structure comprising at least one nitrogen hetero atom and zero to two further hetero atoms selected from S, O and N; R4 and R5 are independently H or C3-C8 cycloalkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C5 alkoxy, C1-C4 alkanoyloxy, C1-C4 alkylthio, amino, carboxy, carbamoyl, cyano, halo, hydroxy, aminomethyl, hydroxymethyl, carboxymethyl, or halo substituted C1-C6 alkyl mercapto, nitro; or R4 and RS join to form a 3-6 membered, optionally substituted ring structure; R6 is 0 or S; Rx is the residue of a natural or unnatural amino acid; and L* is a linker moiety which is ether-, carbonate- or ester-bound to the adjacent oxygen and ester linked to Rx; and pharmaceutically acceptable salts thereof are anti-HIV agents with favourable pharmacokinetic properties.