1206102-06-8

Basic information

• Product Name: 3-Benzyloxy-1-(2,3-dihydroxy-propyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid
• Synonyms: 3-Benzyloxy-1-(2,3-dihydroxy-propyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid;1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid
• CAS NO: 1206102-06-8
• Molecular Formula: C₁₆H₁₇NO₆
• Molecular Weight: 319.30928
• Mol File: 1206102-06-8.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Solubility: DCM, DMSO, Methanol
• CAS DataBase Reference: 3-Benzyloxy-1-(2,3-dihydroxy-propyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Benzyloxy-1-(2,3-dihydroxy-propyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid(1206102-06-8)
• EPA Substance Registry System: 3-Benzyloxy-1-(2,3-dihydroxy-propyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid(1206102-06-8)

Safety Data

• Hazardous Substances Data: 1206102-06-8(Hazardous Substances Data)

Usage

Description

3-Benzyloxy-1-(2,3-dihydroxy-propyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid is a complex organic compound characterized by its unique molecular structure. It is an intermediate in the synthesis of various pharmaceutical compounds, particularly those used in the treatment of viral infections.

Uses

Used in Pharmaceutical Industry:
3-Benzyloxy-1-(2,3-dihydroxy-propyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid is used as an intermediate in the synthesis of Dolutegravir (D528800), a second-generation HIV-1 integrase strand transfer inhibitor. Its role in the production of this medication is crucial, as it helps in the development of a more effective treatment for HIV-1 infections.
Application Reason:
The compound's unique structure allows it to be a key component in the synthesis of Dolutegravir, which is an important drug in the fight against HIV-1. By serving as an intermediate, it contributes to the development of a more potent and targeted treatment option for patients suffering from this viral infection.

Upstream product

• 616-30-8 3-Amino-1,2-propanediol 
• 1229006-11-4 C₂₀H₁₆O₃ 
• 100-44-7 benzyl chloride 
• 500371-01-7 3-(benzyloxy)-4-oxo-4H-pyran-2-carbaldehyde 
• 1206102-05-7 2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one 
• 1206102-04-6 2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one 
• 61049-69-2 3-O-benzylmaltol 
• 100-39-0 benzyl bromide 
• 118-71-8 Maltol 
• 119736-16-2 3-(benzyloxy)-1-((tert-butoxycarbonyl)amino)-4-oxo-1,4-dihydropyridine-2-carboxylic acid ethyl ester 

Downstream Products

• 1206102-07-9 1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid methyl ester 
• 1206102-08-0 methyl 1-(2,2-dihydroxyethyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate 

Relevant articles and documents

Practical and Scalable Synthetic Method for Preparation of Dolutegravir Sodium: Improvement of a Synthetic Route for Large-Scale Synthesis

A practical and scalable synthetic method to obtain dolutegravir sodium (1) was established starting from the readily accessible material maltol (2). This synthetic method includes a scalable oxidation process of maltol and palladium-catalyzed amidation for introduction of an amide moiety, leading to a practical manufacturing method in short synthetic steps. The synthetic method demonstrated herein enables multikilogram scale manufacturing of 1 of high purity.

Improved method for synthesizing dolutegravir

The invention relates to an improved method for synthesizing dolutegravir and belongs to the field of medicinal chemistry. The method takes maltol (compound 1) as a raw material, and a target is synthesized by the following route. The process raw material is cheap and easy to obtain, a reaction solvent can be recycled, the post-treatment operation is simple, the yield and the purity are high, especially the carbamoylation and debenzylation reaction are carried out in one step, the synthesis route is simplified, the cost is reduced, and the large-scale industrial production is facilitated.

(3S,11aR)-6-[(phenylmethyl)oxy]-3-methyl-2,3,11,11a-tetrahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-5,7-dione of the formula P-9 and/or (3S,11aR)-6-[(phenymethyl)oxy]-8-bromo-3-methyl-2,3,11,11a-tetrahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-5,7-dione of the formula P-10

The compounds are intermediates in the preparation of therapeutic agents useful in the treatment of viral infections, particularly HIV infection. The compounds are (3S,11aR)-6-[(phenylmethyl)oxy]-3-methyl-2,3,11,11a-tetrahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-5,7-dione of the formula P-9 and/or (3S,11aR)-6-[(phenylmethyl)oxy]-8-bromo-3-methyl-2,3,11,11a-tetrahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-5,7-dione of the formula P-10.