3-[4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-propionic acid

Base Information

• Chemical Name: 3-[4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-propionic acid
• CAS No.: 160974-83-4
• Molecular Formula: C₂₃H₂₈O₁₂
• Molecular Weight: 496.468

Synonyms:3-[4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-propionic acid

Chemical Property of 3-[4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-propionic acid

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Technology Process of 3-[4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-propionic acid

There total 3 articles about 3-[4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-propionic acid 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:

(E)-3-[4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid benzyl ester → 3-[4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-propionic acid (160974-83-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1248/bpb.18.208

Reference yield:

3-(4'-hydroxyphenyl)-(E)-propenoic acid benzyl ester (61844-62-0) → 3-[4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-propionic acid (160974-83-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Ag₂O / quinoline

2: H₂ / 10 percent Pd-C / tetrahydrofuran / 24 h / 20 °C

With hydrogen; silver(l) oxide; palladium on activated charcoal; In tetrahydrofuran; quinoline; 1: Substitution / 2: Hydrogenolysis;

DOI:10.1248/bpb.18.208

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 3-[4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-propionic acid (160974-83-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Ag₂O / quinoline

2: H₂ / 10 percent Pd-C / tetrahydrofuran / 24 h / 20 °C

With hydrogen; silver(l) oxide; palladium on activated charcoal; In tetrahydrofuran; quinoline; 1: Substitution / 2: Hydrogenolysis;

DOI:10.1248/bpb.18.208

upstream raw materials:

3-(4'-hydroxyphenyl)-(E)-propenoic acid benzyl ester

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(2-hydroxycarbamoyl-ethyl)-phenoxy]-tetrahydro-pyran-3-yl ester

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