methyl 2-(6'-O-benzyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl propionate

Base Information

• Chemical Name: methyl 2-(6'-O-benzyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl propionate
• CAS No.: 478701-16-5
• Molecular Formula: C₂₃H₂₈O₉
• Molecular Weight: 448.47
• Mol file: 478701-16-5.mol

Synonyms:methyl 2-(6'-O-benzyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl propionate

Chemical Property of methyl 2-(6'-O-benzyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-(6'-O-benzyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl propionate

There total 12 articles about methyl 2-(6'-O-benzyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl 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: 77.0%

methyl 2-(2',3',4'-tri-O-acetyl-6'-O-benzyl-β-D-galactopyranosyl-oxy)-3-p-acetyloxyphenyl propionate (478701-09-6) → methyl 2-(6'-O-benzyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl propionate (478701-16-5)

Guidance literature:

With sodium methylate; In methanol;

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

Reference yield:

2,3,4-tri-O-acetyl-6-O-benzyl-α-D-galactopyranosyl bromide (290330-34-6) → methyl 2-(6'-O-benzyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl propionate (478701-16-5)

Guidance literature:

Multi-step reaction with 2 steps

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

2: sodium methoxide / methanol / 7 h / 20 °C

With sodium methylate; silver trifluoromethanesulfonate; 4 A molecular sieve; In methanol; dichloromethane;

DOI:10.1016/j.tet.2005.06.022

Reference yield:

methyl 3-p-hydroxyphenyl-2-t-butyldimethylsiloxy propionate (481072-51-9) → methyl 2-(6'-O-benzyl-β-D-galactopyranosyloxy)-3-p-hydroxyphenyl propionate (478701-16-5)

Guidance literature:

Multi-step reaction with 4 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

4: sodium methoxide / methanol / 7 h / 20 °C

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

DOI:10.1016/j.tet.2005.06.022

upstream raw materials:

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

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

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

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

Downstream raw materials:

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

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