5,8-Dihydroxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one

Base Information

• Chemical Name: 5,8-Dihydroxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one
• CAS No.: 1043-08-9
• Molecular Formula: C₁₈H₁₄O₅
• Molecular Weight: 310.306
• Mol file: 1043-08-9.mol

Synonyms:Osajaxanthone

Chemical Property of 5,8-Dihydroxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one

Chemical Property:

• PSA: 79.90000
• LogP: 3.54160

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 5,8-Dihydroxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one (Osajaxanthone) is a natural xanthone derivative synthesized through a regioselective coupling reaction of 1,3,7-trihydroxyxanthone with prenal under mild conditions using calcium hydroxide, achieving a high yield of 75%. This method provides an efficient and selective route to access Osajaxanthone, demonstrating significant improvements over prior synthetic approaches. The compound's structure was confirmed by analytical and spectral data, highlighting its relevance as a target in natural product synthesis.

Technology Process of 5,8-Dihydroxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one

There total 7 articles about 5,8-Dihydroxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

3,3-dimethyl acrylaldehyde (107-86-8) + gentitein (529-49-7) → osajaxanthone (1043-08-9)

Guidance literature:

With calcium hydroxide; In methanol; at 20 ℃; for 36h;

DOI:10.1021/jo0606655

Reference yield:

(2,5-dibenzyloxyphenyl)(2,4,6-trimethoxyphenyl)methanone (900501-59-9) → osajaxanthone (1043-08-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / H₂ / Pd/C / methanol / 24 h / 20 °C / 3361.46 Torr

2: 100 percent / KOH / methanol / 12 h / Heating

3: 82 percent / BBr₃ / CH₂Cl₂ / -78 - 20 °C

4: 75 percent / Ca(OH)2 / methanol / 36 h / 20 °C

With calcium hydroxide; potassium hydroxide; hydrogen; boron tribromide; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/jo0606655

Reference yield:

Methyl 2,5-dihydroxybenzoate (2150-46-1) → osajaxanthone (1043-08-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 98 percent / K₂CO₃ / acetone / 6 h / Heating

2.1: n-BuLi / tetrahydrofuran / 0.75 h / -78 °C

2.2: 75 percent / tetrahydrofuran / 0.5 h / -78 °C

3.1: 100 percent / H₂ / Pd/C / methanol / 24 h / 20 °C / 3361.46 Torr

4.1: 100 percent / KOH / methanol / 12 h / Heating

5.1: 82 percent / BBr₃ / CH₂Cl₂ / -78 - 20 °C

6.1: 75 percent / Ca(OH)2 / methanol / 36 h / 20 °C

With calcium hydroxide; potassium hydroxide; n-butyllithium; hydrogen; boron tribromide; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1021/jo0606655

upstream raw materials:

3,3-dimethyl acrylaldehyde

gentitein

(2,5-dihydroxyphenyl)(2,4,6-trimethoxyphenyl)methanone

(2,5-dibenzyloxyphenyl)(2,4,6-trimethoxyphenyl)methanone

Refernces

Facile synthesis of 1,3,7-trihydroxyxanthone and its regioselective coupling reactions with prenal: Simple and efficient access to osajaxanthone and nigrolineaxanthone F

10.1021/jo0606655

The research aims to develop a simple and efficient method for synthesizing 1,3,7-trihydroxyxanthone and its subsequent regioselective coupling reactions with prenal to exclusively produce the natural products osajaxanthone and nigrolineaxanthone F. The study describes a five-step synthesis of 1,3,7-trihydroxyxanthone starting from 1,3,5-trimethoxybenzene, involving NBS-induced bromination, lithiation, benzoylation, selective deprotection, intramolecular cyclization, and demethylation, achieving an overall yield of 62%. The regioselective coupling reactions with prenal were conducted under different conditions: at room temperature with calcium hydroxide yielding osajaxanthone (75% yield) and under thermal conditions at 140-150 °C yielding nigrolineaxanthone F (98% yield). The study concludes that this approach offers a straightforward and efficient route to these xanthones, with high yields and selectivity, providing a significant improvement over previous methods. The structures of the compounds were confirmed using analytical and spectral data, including X-ray crystallography.