Carbonic acid (2R,3S,4S,5R,6S)-6-[3-allyloxy-2-(3-benzofuran-5-yl-propionyl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester methyl ester

Base Information

• Chemical Name: Carbonic acid (2R,3S,4S,5R,6S)-6-[3-allyloxy-2-(3-benzofuran-5-yl-propionyl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester methyl ester
• CAS No.: 217634-89-4
• Molecular Formula: C₂₈H₃₀O₁₁
• Molecular Weight: 542.54

Synonyms:Carbonic acid (2R,3S,4S,5R,6S)-6-[3-allyloxy-2-(3-benzofuran-5-yl-propionyl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester methyl ester

Chemical Property of Carbonic acid (2R,3S,4S,5R,6S)-6-[3-allyloxy-2-(3-benzofuran-5-yl-propionyl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester methyl ester

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Technology Process of Carbonic acid (2R,3S,4S,5R,6S)-6-[3-allyloxy-2-(3-benzofuran-5-yl-propionyl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester methyl ester

There total 2 articles about Carbonic acid (2R,3S,4S,5R,6S)-6-[3-allyloxy-2-(3-benzofuran-5-yl-propionyl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester methyl ester 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: 91.0%

methyl chloroformate (79-22-1) + 6'-allyloxy-2-(benzofuran-5-yl)-2'-hydroxypropiophenone 2'-O-β-D-glucopyranoside (217634-73-6) → Carbonic acid (2R,3S,4S,5R,6S)-6-[3-allyloxy-2-(3-benzofuran-5-yl-propionyl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester methyl ester (217634-89-4)

Guidance literature:

With 2,4,6-trimethyl-pyridine; In dichloromethane; at -40 - 20 ℃; for 4.5h;

DOI:10.1248/cpb.46.1545

Reference yield:

2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]-furanyl)propiophenone (174456-32-7) → Carbonic acid (2R,3S,4S,5R,6S)-6-[3-allyloxy-2-(3-benzofuran-5-yl-propionyl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester methyl ester (217634-89-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / K₂CO₃ / acetone / 5 h / Heating

2: 91 percent / 2,4,6-collidine / CH₂Cl₂ / 4.5 h / -40 - 20 °C

With 2,4,6-trimethyl-pyridine; potassium carbonate; In dichloromethane; acetone;

DOI:10.1248/cpb.46.1545

Reference yield: 96.0%

Carbonic acid (2R,3S,4S,5R,6S)-6-[3-allyloxy-2-(3-benzofuran-5-yl-propionyl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester methyl ester (217634-89-4) → 2-(benzofuran-5-yl)-2',6'-dihydroxypropiophenone 2'-O-(6-O-methoxycarbonyl-β-D-glucopyranoside)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; ammonium formate; In acetonitrile; for 2h; Heating;

DOI:10.1248/cpb.46.1545

upstream raw materials:

methyl chloroformate

6'-allyloxy-2-(benzofuran-5-yl)-2'-hydroxypropiophenone 2'-O-β-D-glucopyranoside

2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]-furanyl)propiophenone

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