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

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

Uses

1. Used in Organic Synthesis:
N-[(Phenylmethoxy)carbonyl]-L-valine 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for the formation of new chemical bonds and the creation of a wide range of molecules with different properties and applications.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-[(Phenylmethoxy)carbonyl]-L-valine 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester is used as a building block for the development of new drugs. Its chemical properties make it a valuable component in the design and synthesis of novel therapeutic agents, potentially targeting a variety of medical conditions.
3. Used in Research and Development:
N-[(Phenylmethoxy)carbonyl]-L-valine 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester is also utilized in research and development settings, where it can be employed to study the mechanisms of various biological processes and to develop new methodologies for chemical synthesis. Its unique structure and reactivity make it an interesting subject for scientific investigation and potential innovation in the field of chemistry.

Upstream product

• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 88110-89-8 9-<(1-acetoxy-2-hydroxymethyl)ethoxymethyl>guanine 
• 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 

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.

A method for preparing valganciclovir hydrochloride

The invention discloses a method for preparing valganciclovir hydrochloride I. The method comprises the following steps of: 1, dissolving phosphorus oxychloride into an inert solvent, and performing a reaction of the mixture and the alcoholic liquor to obtain phosphoryl halide II; 2, performing a reaction of ganciclovir and the phosphoryl halide II obtained in the step to obtain ganciclovir monoester III; 3, esterfying the ganciclovir monoester III in the step 2 and N-carbobenzoxy-L-valine to obtain ganciclovir diester IV; 4, acidizing the ganciclovir diester IV in the step 3 for dephosphorylation to obtain N-carbobenzoxy-L-valine ganciclovir monoester V; and 5, performing a hydrogenation reaction on the product in the step 4 to prepare the valganciclovir hydrochloride I. By the method, the ganciclovir monoester with high purity and yield can be produced, the post-processing is easy, and the post-processing difficulty is reduced.

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 valganciclovir

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.

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.

PREPARATION OF ESTERS OF PURINE DERIVATIVES

The present invention relates to the preparation of esters of purine derivatives and enantiomerically pure esters of purine derivatives or pharmaceutically acceptable salts thereof.