4-benzyloxy-2-hydroxy-6-(4-methoxymethoxybenzoyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone

Base Information

• Chemical Name: 4-benzyloxy-2-hydroxy-6-(4-methoxymethoxybenzoyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone
• CAS No.: 791601-75-7
• Molecular Formula: C₅₈H₅₆O₁₂
• Molecular Weight: 945.075
• Mol file: 791601-75-7.mol

Synonyms:4-benzyloxy-2-hydroxy-6-(4-methoxymethoxybenzoyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone

Chemical Property of 4-benzyloxy-2-hydroxy-6-(4-methoxymethoxybenzoyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-benzyloxy-2-hydroxy-6-(4-methoxymethoxybenzoyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone

There total 3 articles about 4-benzyloxy-2-hydroxy-6-(4-methoxymethoxybenzoyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone 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: 92.0%

4-(methoxymethoxy)benzoic acid (25458-44-0) + 1-{4-(benzyloxy)-2,6-dihydroxy-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl]phenyl}ethanone (163395-92-4) → 4-benzyloxy-2-hydroxy-6-(4-methoxymethoxybenzoyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone (791601-75-7)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.tet.2004.08.015

Reference yield:

1-[4-(benzyloxy)-2,6-dihydroxyphenyl]ethanone (35028-02-5) → 4-benzyloxy-2-hydroxy-6-(4-methoxymethoxybenzoyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone (791601-75-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / TMSOTf / CH₂Cl₂ / 18 h / 20 °C

2: 92 percent / DCC; DMAP / CH₂Cl₂ / 12 h / 20 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1016/j.tet.2004.08.015

Reference yield:

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (74808-09-6) → 4-benzyloxy-2-hydroxy-6-(4-methoxymethoxybenzoyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone (791601-75-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / TMSOTf / CH₂Cl₂ / 18 h / 20 °C

2: 92 percent / DCC; DMAP / CH₂Cl₂ / 12 h / 20 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1016/j.tet.2004.08.015

upstream raw materials:

4-(methoxymethoxy)benzoic acid

1-{4-(benzyloxy)-2,6-dihydroxy-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl]phenyl}ethanone

1-[4-(benzyloxy)-2,6-dihydroxyphenyl]ethanone

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

Downstream raw materials:

6-(β-D-glucopyranosyl)-5,7-dihydroxy-2-(4-methoxymethoxyphenyl)-4H-1-benzopyran-4-one

7-benzyloxy-5-hydroxy-2-(4-methoxymethoxyphenyl)-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one