194154-40-0

Basic information

• Product Name: N-[(Phenylmethoxy)carbonyl]-L-valine 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester
• Synonyms: 2-(2-Amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-3-hydroxy-1-propyl N-(benzyloxycarbonyl)-L-valinate;Cbz-Valine ganciclovir;N-[(Phenylmethoxy)carbonyl]-L-valine 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester;BZ-L-Valganciclovir;CBZ-Vaganciclovir;N-(benzyloxycarbonyl)-L-valinate;[2-[(2-amino-6-oxo-3H-purin-9-yl)methoxy]-3-hydroxypropyl] (2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoate
• CAS NO: 194154-40-0
• Molecular Formula: C₂₂H₂₈N₆O₇
• Molecular Weight: 488.49
• EINECS: 1312995-182-4
• Product Categories: Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals
• Mol File: 194154-40-0.mol
• Article Data: 6

Chemical Properties

• Appearance: White solid
• Density: 1.46
• Storage Temp.: -20?C Freezer
• PKA: 9.32±0.20(Predicted)
• CAS DataBase Reference: N-[(Phenylmethoxy)carbonyl]-L-valine 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(Phenylmethoxy)carbonyl]-L-valine 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester(194154-40-0)
• EPA Substance Registry System: N-[(Phenylmethoxy)carbonyl]-L-valine 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester(194154-40-0)

Safety Data

• Hazardous Substances Data: 194154-40-0(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

N-Carbobenzyloxy-L-valinyl-ganciclovir (cas# 194154-40-0) is a compound useful in organic synthesis.

Upstream product

• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 108436-36-8 9-<<2-chloro-1-(hydroxymethyl)ethoxy>methyl>guanine 
• 130914-77-1 2-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-1,3-propanediyl bis(N-((benzyloxy)carbonyl)-L-valinate) 
• 82410-32-0 ganciclovir 
• 194159-22-3 2-(2-amino-1,6 dihydro-6-oxo-purine-9-yl)-methoxy-3 acetoxy-1-propyl-N-(benzyloxycarbonyl)-L-valinate 
• 88110-89-8 9-<(1-acetoxy-2-hydroxymethyl)ethoxymethyl>guanine 

Downstream Products

• 175865-59-5 2-(2-amino-1,6-dihydro-6-oxo-purine-9-yl)-methoxy-3-hydroxy-1-propyl-L-valinate hydrochloride 
• 175865-59-5 valganciclovir hydrochloride 

Relevant articles and documents

Synthetic method of valganciclovir hydrochloride

The invention discloses a method for synthesizing valganciclovir hydrochloride, which comprises the following steps: with 1,3-dichloro-2-acetoxymethoxypropane as an initial raw material, preparing monochlorinated ganciclovir, and carrying out esterification, hydrolysis and deprotection salification to finally obtain the valganciclovir hydrochloride. The invention provides a synthesis method of siganciclovir hydrochloride, which avoids the problem of separation and conversion of N-7 and N-9 isomers in the diacetyl guanine condensation process. The method directly synthesizes monochlorinated ganciclovir without using ganciclovir, instead of the synthesis of monoacetyl ganciclovir in the prior art, so that the method avoids the problem of diester compound separation caused by ganciclovir residues, has the advantages of short process steps, simple operation, convenient purification and low cost, is beneficial to industrial production, and is suitable for synthesis of valganciclovir hydrochloride.

PREPARATION OF VALGANCICLOVIR AND ITS SALTS

The application relates to processes for preparing valganciclovir and pharmaceutically acceptable salts thereof, as well as intermediates for the processes. valganciclovir hydrochloride is represented by Formula II.

Preparation of ester of purine derivatives

A process for the preparation of valganciclovir with triacetyl ganciclovir (V) as a starting material, comprising the following steps: selective hydrolysis, reacting with a coupling agent and a solvent, followed by hydrolysis under basic conditions and hydrogenolysis in the presence of a catalyst.