methyl 2-(2',3',4'-tri-O-acetyl-6'-O-benzyl-β-D-galactopyranosyl-oxy)-3-p-acetyloxyphenyl propionate

Base Information

• Chemical Name: methyl 2-(2',3',4'-tri-O-acetyl-6'-O-benzyl-β-D-galactopyranosyl-oxy)-3-p-acetyloxyphenyl propionate
• CAS No.: 478701-09-6
• Molecular Formula: C₃₁H₃₆O₁₃
• Molecular Weight: 616.619
• Mol file: 478701-09-6.mol

Synonyms:methyl 2-(2',3',4'-tri-O-acetyl-6'-O-benzyl-β-D-galactopyranosyl-oxy)-3-p-acetyloxyphenyl propionate

Chemical Property of methyl 2-(2',3',4'-tri-O-acetyl-6'-O-benzyl-β-D-galactopyranosyl-oxy)-3-p-acetyloxyphenyl propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-(2',3',4'-tri-O-acetyl-6'-O-benzyl-β-D-galactopyranosyl-oxy)-3-p-acetyloxyphenyl propionate

There total 10 articles about methyl 2-(2',3',4'-tri-O-acetyl-6'-O-benzyl-β-D-galactopyranosyl-oxy)-3-p-acetyloxyphenyl propionate 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: 55.0%

2,3,4-tri-O-acetyl-6-O-benzyl-α-D-galactopyranosyl bromide (290330-34-6) + methyl 3-p-acetoxyphenyl-2-hydroxy propionate (77573-21-8) → methyl 2-(2',3',4'-tri-O-acetyl-6'-O-benzyl-β-D-galactopyranosyl-oxy)-3-p-acetyloxyphenyl propionate (478701-09-6)

Guidance literature:

With silver trifluoromethanesulfonate; In dichloromethane;

DOI:10.1016/S0040-4039(02)01460-0

Reference yield:

methyl 3-p-hydroxyphenyl-2-t-butyldimethylsiloxy propionate (481072-51-9) → methyl 2-(2',3',4'-tri-O-acetyl-6'-O-benzyl-β-D-galactopyranosyl-oxy)-3-p-acetyloxyphenyl propionate (478701-09-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / pyridine

2: 98 percent / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran

3: AgOTf / molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / -30 - 20 °C

With pyridine; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; acetic acid; 4 A molecular sieve; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2005.06.022

Reference yield:

methyl 3-p-acetoxyphenyl-2-t-butyldimethylsiloxy propionate (864070-64-4) → methyl 2-(2',3',4'-tri-O-acetyl-6'-O-benzyl-β-D-galactopyranosyl-oxy)-3-p-acetyloxyphenyl propionate (478701-09-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran

2: AgOTf / molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / -30 - 20 °C

With tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; acetic acid; 4 A molecular sieve; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2005.06.022

upstream raw materials:

2,3,4-tri-O-acetyl-6-O-benzyl-α-D-galactopyranosyl bromide

methyl 3-p-acetoxyphenyl-2-hydroxy propionate

methyl 3-p-hydroxyphenyl-2-t-butyldimethylsiloxy propionate

methyl 3-p-acetoxyphenyl-2-t-butyldimethylsiloxy propionate

Downstream raw materials:

methyl 2-(6'-O-benzyl-2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl propionate

methyl 2-(6'-O-acetyl-2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl propionate

methyl 2-(2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl propionate

methyl (Z)-2-(6'-O-acetyl-2',3',4'-tri-O-t-butyldimethylsilyl-β-D-galactopyranosyloxy)-3-p-t-butyldimethylsiloxyphenyl acrylate