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

Base Information

• Chemical Name: (E)-3-[4-((2S,3R,4S,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid methyl ester
• CAS No.: 478380-98-2
• Molecular Formula: C₂₄H₂₈O₁₂
• Molecular Weight: 508.479
• Mol file: 478380-98-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (E)-3-[4-((2S,3R,4S,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid 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: 92.0%

O-(4-iodophenyl)-(2,3,4,6-O-tetraacetyl)-β-D-galactopyranose (52571-61-6,101685-91-0) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (E)-3-[4-((2S,3R,4S,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid methyl ester (478380-98-2)

Guidance literature:

With triethylamine; tris-(o-tolyl)phosphine; palladium diacetate; In acetonitrile; at 70 ℃;

DOI:10.1055/s-2003-43376

Reference yield: 52.0%

methyl 4-hydroxycinnamate (3943-97-3) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → (E)-3-[4-((2S,3R,4S,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid methyl ester (478380-98-2) + (E)-3-[4-((2R,3R,4S,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid methyl ester

Guidance literature:

With silver trifluoromethanesulfonate; In dichloromethane;

DOI:10.1016/S0040-4039(02)01848-8

Reference yield:

phenyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-72-2) → (E)-3-[4-((2S,3R,4S,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid methyl ester (478380-98-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / ceric ammonium nitrate; n-Bu₄NI / acetonitrile / 24 h / 70 °C

2: 92 percent / P(o-tol)3; Et₃N / Pd(OAc)2 / acetonitrile / 70 °C

With ammonium cerium(IV) nitrate; tetra-(n-butyl)ammonium iodide; triethylamine; tris-(o-tolyl)phosphine; palladium diacetate; In acetonitrile; 2: Heck reaction;

DOI:10.1055/s-2003-43376

upstream raw materials:

methyl 4-hydroxycinnamate

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

O-(4-iodophenyl)-(2,3,4,6-O-tetraacetyl)-β-D-galactopyranose

acrylic acid methyl ester