1-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl]-3,4-dimethyl-pyrrole-2,5-dione

Base Information

• Chemical Name: 1-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl]-3,4-dimethyl-pyrrole-2,5-dione
• CAS No.: 640273-51-4
• Molecular Formula: C₁₉H₂₃NO₈
• Molecular Weight: 393.394
• Mol file: 640273-51-4.mol

Synonyms:1-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl]-3,4-dimethyl-pyrrole-2,5-dione

Chemical Property of 1-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl]-3,4-dimethyl-pyrrole-2,5-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl]-3,4-dimethyl-pyrrole-2,5-dione

There total 1 articles about 1-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl]-3,4-dimethyl-pyrrole-2,5-dione 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: 46.0%

4-methoxy-phenol (150-76-5) + 1,3,4,6-tetra-O-acetyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranose → 1-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl]-3,4-dimethyl-pyrrole-2,5-dione (640273-51-4)

Guidance literature:

4-methoxy-phenol; 1,3,4,6-tetra-O-acetyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranose; With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In 1,2-dichloro-ethane;

With methanol; sodium methylate;

DOI:10.1021/ol035882w

Reference yield: 81.0%

benzaldehyde dimethyl acetal (1125-88-8) + 1-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl]-3,4-dimethyl-pyrrole-2,5-dione (640273-51-4) → 1-[(2R,4aR,6S,7R,8R,8aS)-8-Hydroxy-6-(4-methoxy-phenoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-3,4-dimethyl-pyrrole-2,5-dione (640273-52-5)

Guidance literature:

With camphor-10-sulfonic acid; In acetonitrile;

DOI:10.1021/ol035882w

Reference yield:

1-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl]-3,4-dimethyl-pyrrole-2,5-dione (640273-51-4) → Sulfuric acid mono-[(2R,4aR,6S,7R,8R,8aR)-7-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-6-(4-methoxy-phenoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl] ester

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / CSA / acetonitrile

2: sulfur trioxide-trimethylamine complex / dimethylformamide / 50 °C

With camphor-10-sulfonic acid; sulfur trioxide trimethylamine complex; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ol035882w

upstream raw materials:

4-methoxy-phenol

Downstream raw materials:

1-[(2R,4aR,6S,7R,8R,8aS)-8-Hydroxy-6-(4-methoxy-phenoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-3,4-dimethyl-pyrrole-2,5-dione