2'-(2,3-di-O-acetyl-β-D-glucopyranosyloxy)-6'-acetoxy-3-(5-benzo[b]furanyl)propiophenone

Base Information

• Chemical Name: 2'-(2,3-di-O-acetyl-β-D-glucopyranosyloxy)-6'-acetoxy-3-(5-benzo[b]furanyl)propiophenone
• CAS No.: 174456-37-2
• Molecular Formula: C₂₉H₃₀O₁₂
• Molecular Weight: 570.55

Synonyms:2'-(2,3-di-O-acetyl-β-D-glucopyranosyloxy)-6'-acetoxy-3-(5-benzo[b]furanyl)propiophenone

Chemical Property of 2'-(2,3-di-O-acetyl-β-D-glucopyranosyloxy)-6'-acetoxy-3-(5-benzo[b]furanyl)propiophenone

Chemical Property:

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Technology Process of 2'-(2,3-di-O-acetyl-β-D-glucopyranosyloxy)-6'-acetoxy-3-(5-benzo[b]furanyl)propiophenone

There total 2 articles about 2'-(2,3-di-O-acetyl-β-D-glucopyranosyloxy)-6'-acetoxy-3-(5-benzo[b]furanyl)propiophenone 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:

2'-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyloxy)-6'-acetoxy-3-(5-benzo-[b]furanyl)propiophenone (174456-59-8) → 2'-(2,3-di-O-acetyl-β-D-glucopyranosyloxy)-6'-acetoxy-3-(5-benzo[b]furanyl)propiophenone (174456-37-2)

Guidance literature:

With acetic acid; at 70 ℃; for 2h; Yield given;

DOI:10.1248/cpb.46.1545

Reference yield:

2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]-furanyl)propiophenone (174456-32-7) → 2'-(2,3-di-O-acetyl-β-D-glucopyranosyloxy)-6'-acetoxy-3-(5-benzo[b]furanyl)propiophenone (174456-37-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / p-TsOH*H₂O / CH₂Cl₂; dioxane / 15 h / Ambient temperature

2: pyridine / 3 h / Ambient temperature

3: aq. AcOH / 2 h / 70 °C

With pyridine; toluene-4-sulfonic acid; acetic acid; In 1,4-dioxane; dichloromethane;

DOI:10.1248/cpb.46.1545

Reference yield: 69.0%

Dimethoxymethane (109-87-5) + 2'-(2,3-di-O-acetyl-β-D-glucopyranosyloxy)-6'-acetoxy-3-(5-benzo[b]furanyl)propiophenone (174456-37-2) → 6'-acetoxy-2-(benzofuran-5-yl)-2'-hydroxypropiophenone 2'-O-(2,3-O-diacetyl-6-O-methoxymethyl-β-D-glucopyranoside) (189576-63-4)

Guidance literature:

With toluene-4-sulfonic acid; lithium bromide; at 20 - 55 ℃; for 5.5h;

DOI:10.1248/cpb.46.1545

upstream raw materials:

2'-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyloxy)-6'-acetoxy-3-(5-benzo-[b]furanyl)propiophenone

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

Downstream raw materials:

6'-acetoxy-2-(benzofuran-5-yl)-2'-hydroxypropiophenone 2'-O-(2,3-O-diacetyl-6-O-methoxymethyl-β-D-glucopyranoside)

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