methyl (Z)-2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate

Base Information

Chemical Name:methyl (Z)-2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate
CAS No.:223930-90-3
Molecular Formula:C₂₄H₂₈O₁₃
Molecular Weight:524.479
Hs Code.:

Synonyms:methyl (Z)-2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate

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Chemical Property of methyl (Z)-2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate

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Technology Process of methyl (Z)-2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate

There total 7 articles about methyl (Z)-2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate 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: 47.0%

: 223930-88-9
methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylpropionate

: 223930-90-3
methyl (Z)-2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate

: (E)-3-(4-Hydroxy-phenyl)-2-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid methyl ester

Guidance literature:: methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylpropionate; With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In toluene; for 144h; Heating;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 5 ℃; for 0.5h;
DOI:10.1016/S0040-4020(99)00618-3

Reference yield:

: 128316-64-3,481072-37-1
(+/-)-methyl 3-p-benzyloxyphenyl-2-hydroxypropionate

: 223930-90-3
methyl (Z)-2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate

Guidance literature:: Multi-step reaction with 5 steps

1: 67 percent / AgOTf; molecular sieves, 4 Angstroem / CH₂Cl₂

2: 100 percent / H₂ / Pd-C / methanol; ethyl acetate

3: 100 percent / imidazole; DMAP / dimethylformamide

4: DDQ / toluene

5: TBAF / tetrahydrofuran

With 1H-imidazole; dmap; molecular sieve; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; silver trifluoromethanesulfonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(02)01770-7

Reference yield:

: 223930-86-7
methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-benzyloxyphenyl-propionate

: 223930-90-3
methyl (Z)-2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl-2-acrylate

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / H₂ / Pd-C / methanol; ethyl acetate

2: 100 percent / imidazole; DMAP / dimethylformamide

3: DDQ / toluene

4: TBAF / tetrahydrofuran

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; hydrogen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(02)01770-7