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

Base Information

• Chemical Name: 5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-7-methoxyflavan
• CAS No.: 749256-76-6
• Molecular Formula: C₅₄H₅₄O₁₁
• Molecular Weight: 879.016
• Mol file: 749256-76-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzyl-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:

4'-acetoxy-5-hydroxy-7-methoxynaringenin (88607-74-3) + 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride (78153-79-4,89025-46-7,94898-42-7,94898-43-8,101966-50-1,143615-35-4,122741-44-0) + acetyl chloride (75-36-5) → 4'-acetoxy-5-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-7-methoxyflavan + 4'-acetoxy-5-O-(2,3,4,6-tetra-O-benzyl-βa-D-glucopyranosyl)-7-methoxyflavan + 4'-acetoxy-6-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-hydroxy-7-methoxyflavan + 5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-7-methoxyflavan (749256-76-6)

Guidance literature:

4'-acetoxy-5-hydroxy-7-methoxynaringenin; 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride; With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 1.5h;

acetyl chloride; With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1021/jo0494681

Reference yield:

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

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; ethyl acetate; at 20 ℃; for 1.5h; under 760 Torr;

DOI:10.1021/jo0494681

Reference yield:

5,4'-diacetoxy-6-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-7-methoxyflavan (749256-76-6) → Flavocommelin (16049-42-6)

Guidance literature:

Multi-step reaction with 7 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

3: 43 percent / ceric ammonium nitrite; acetic acid / acetonitrile; H₂O / 0.5 h / 50 °C

4: 80 percent / AcCl / methanol; CHCl₃ / 2 h / 20 °C

5: 84 percent / 2,6-di-tert-butyl-4-methylpyridine; BF₃*Et₂O / CH₂Cl₂ / 1 h / 20 °C

6: 83 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / chlorobenzene / 13 h / 140 °C

7: 90 percent / KOH / methanol; tetrahydrofuran / 16 h / 20 °C

With pyridine; dmap; potassium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; hydrogen; acetic acid; acetyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; ethyl acetate; chlorobenzene; acetonitrile;

DOI:10.1021/jo0494681

upstream raw materials:

4'-acetoxy-5-hydroxy-7-methoxynaringenin

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride

acetyl chloride

Downstream raw materials:

Flavocommelin

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

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

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