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

Base Information

Chemical Name:methyl (Z)-2-(6'-iodo-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate
CAS No.:295797-79-4
Molecular Formula:C₂₂H₂₅IO₁₁
Molecular Weight:592.338
Hs Code.:

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

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

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

There total 5 articles about methyl (Z)-2-(6'-iodo-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate 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: 54.0%

: 295797-72-7
methyl (Z)-2-(6'-O-p-toluenesulfonyl-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate

: 295797-79-4
methyl (Z)-2-(6'-iodo-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate

Guidance literature:: With sodium iodide; In N,N-dimethyl-formamide; at 80 ℃; for 48h;
DOI:10.1016/S0040-4020(00)00421-X

Reference yield:

: 295797-77-2
(Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid methyl ester

: 295797-79-4
methyl (Z)-2-(6'-iodo-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate

Guidance literature:: Multi-step reaction with 4 steps

1: 67 percent / pyridine / 5 h / 20 °C

2: 100 percent / pyridine / 20 °C

3: 100 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

4: 54 percent / NaI / dimethylformamide / 48 h / 80 °C

With pyridine; tetrabutyl ammonium fluoride; sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Tosylation / 2: Acetylation / 3: Substitution / 4: Substitution;
DOI:10.1016/S0040-4020(00)00421-X

Reference yield:

: 223930-89-0
(Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-acrylic acid methyl ester

: 295797-79-4
methyl (Z)-2-(6'-iodo-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / NaOMe / methanol / 3 h

2: 67 percent / pyridine / 5 h / 20 °C

3: 100 percent / pyridine / 20 °C

4: 100 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

5: 54 percent / NaI / dimethylformamide / 48 h / 80 °C

With pyridine; tetrabutyl ammonium fluoride; sodium methylate; sodium iodide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Deacetylation / 2: Tosylation / 3: Acetylation / 4: Substitution / 5: Substitution;
DOI:10.1016/S0040-4020(00)00421-X