5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavan

Base Information

• Chemical Name: 5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavan
• CAS No.: 749256-77-7
• Molecular Formula: C₅₄H₄₆O₁₅
• Molecular Weight: 934.95

Synonyms:5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavan

Chemical Property of 5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavan

Chemical Property:

Purity/Quality:

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Technology Process of 5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavan

There total 2 articles about 5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavan 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:

5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-7-methoxyflavan (749256-76-6) → 5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavan (749256-77-7)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd(OH)2/C / methanol; ethyl acetate / 1.5 h / 20 °C / 760 Torr

2: 4-dimethylaminopyridine; pyridine / 1 h / 60 °C

With pyridine; dmap; hydrogen; palladium dihydroxide; In methanol; ethyl acetate;

DOI:10.1021/jo0494681

Reference yield:

benzoyl chloride (98-88-4) + Acetic acid 2-(4-acetoxy-phenyl)-7-methoxy-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-chroman-5-yl ester → 5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavan (749256-77-7)

Guidance literature:

With pyridine; dmap; at 60 ℃; for 1h;

DOI:10.1021/jo0494681

Reference yield: 43.0%

5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavan (749256-77-7) → 5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavanone (749256-78-8)

Guidance literature:

With ammonium cerium(IV) nitrate; acetic acid; In water; acetonitrile; at 50 ℃; for 0.5h;

DOI:10.1021/jo0494681

upstream raw materials:

benzoyl chloride

5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-7-methoxyflavan

Downstream raw materials:

5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavanone

Flavocommelin

5-acetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-7-methoxyflavanone

5-acetoxy-6-C-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranozyl)-7-methoxyflavone

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