methyl (Z)-2-(6'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate

Base Information

• Chemical Name: methyl (Z)-2-(6'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate
• CAS No.: 295797-74-9
• Molecular Formula: C₁₆H₁₉N₃O₈
• Molecular Weight: 381.342
• Mol file: 295797-74-9.mol

Synonyms:methyl (Z)-2-(6'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate

Chemical Property of methyl (Z)-2-(6'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (Z)-2-(6'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate

There total 6 articles about methyl (Z)-2-(6'-azido-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: 84.0%

methyl (Z)-2-(6'-azido-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate (295797-73-8) → methyl (Z)-2-(6'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate (295797-74-9)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/S0040-4039(00)00394-4

Reference yield:

(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 (223930-89-0) → methyl (Z)-2-(6'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate (295797-74-9)

Guidance literature:

Multi-step reaction with 6 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

6: 84 percent / NaOMe / methanol / 0.5 h

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 / 6: Deacetylation;

DOI:10.1016/S0040-4020(00)00421-X

Reference yield:

methyl (Z)-2-(6'-O-p-toluenesulfonyl-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate (295797-72-7) → methyl (Z)-2-(6'-azido-β-D-galactopyranosyloxy)-3-p-hydroxyphenylacrylate (295797-74-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / NaN₃; 15-crown-5 / dimethylformamide / 48 h / 70 °C

2: 84 percent / NaOMe / methanol / 0.5 h

With sodium azide; 15-crown-5; sodium methylate; In methanol; N,N-dimethyl-formamide; 1: Substitution / 2: Deacetylation;

DOI:10.1016/S0040-4020(00)00421-X

upstream raw materials:

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

(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

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

(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

Downstream raw materials:

methyl (Z)-2-[6'-(N-benzyloxycarbonylglycylamino)-β-D-galactopyranosyloxy]-3-p-hydroxyphenylacrylate