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

Base Information

• Chemical Name: methyl (Z)-2-(6'-O-p-toluenesulfonyl-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylacrylate
• CAS No.: 295797-71-6
• Molecular Formula: C₃₅H₄₆O₁₄SSi
• Molecular Weight: 750.893
• Mol file: 295797-71-6.mol

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

Chemical Property of methyl (Z)-2-(6'-O-p-toluenesulfonyl-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylacrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (Z)-2-(6'-O-p-toluenesulfonyl-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylacrylate

There total 5 articles about methyl (Z)-2-(6'-O-p-toluenesulfonyl-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylacrylate 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: 100.0%

acetic anhydride (108-24-7) + (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 (295797-78-3) → methyl (Z)-2-(6'-O-p-toluenesulfonyl-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylacrylate (295797-71-6)

Guidance literature:

With pyridine;

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

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / NaOMe / methanol / 3 h

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

3: 100 percent / pyridine / 20 °C

With pyridine; sodium methylate; In methanol; 1: Deacetylation / 2: Tosylation / 3: Acetylation;

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

Reference yield:

(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 (295797-77-2) → methyl (Z)-2-(6'-O-p-toluenesulfonyl-2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsilyloxyphenylacrylate (295797-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: pyridine

With pyridine;

DOI:10.1246/cl.2002.1118

upstream raw materials:

acetic anhydride

(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

p-toluenesulfonyl chloride

(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

Downstream raw materials:

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

(R)-3-(4-Hydroxy-phenyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yloxy]-propionic acid methyl ester

(Z)-2-((2S,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-3-(4-hydroxy-phenyl)-acrylic acid methyl ester

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