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

Base Information

Chemical Name:methyl (Z)-2-(6'-azido-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate
CAS No.:295797-73-8
Molecular Formula:C₂₂H₂₅N₃O₁₁
Molecular Weight:507.454
Hs Code.:

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

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

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

There total 5 articles about methyl (Z)-2-(6'-azido-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: 63.0%

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

: 295797-73-8
methyl (Z)-2-(6'-azido-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate

Guidance literature:: With sodium azide; 15-crown-5; In N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)00394-4

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

: 295797-73-8
methyl (Z)-2-(6'-azido-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: 63 percent / NaN₃; 15-crown-5 / dimethylformamide / 48 h / 70 °C

With pyridine; sodium azide; 15-crown-5; tetrabutyl ammonium fluoride; sodium methylate; 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

Reference yield:

: 295797-71-6
methyl (Z)-2-(6'-O-p-toluenesulfonyl-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylacrylate

: 295797-73-8
methyl (Z)-2-(6'-azido-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

2: 63 percent / NaN₃; 15-crown-5 / dimethylformamide / 48 h / 70 °C

With sodium azide; 15-crown-5; tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Substitution / 2: Substitution;
DOI:10.1016/S0040-4020(00)00421-X