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

Base Information

• Chemical Name: 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
• CAS No.: 163395-92-4
• Molecular Formula: C₄₉H₄₈O₉
• Molecular Weight: 780.915
• Mol file: 163395-92-4.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 2 articles about 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 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: 74.0%

1-[4-(benzyloxy)-2,6-dihydroxyphenyl]ethanone (35028-02-5) + 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (74808-09-6) → 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)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 30 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ol900689m

Reference yield: 57.0%

4-benzyloxy-6-hydroxy-2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)acetophenone → 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)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 12h; Ambient temperature;

Reference yield: 95.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 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) → C65H66O9Si (1064179-44-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol900689m

upstream raw materials:

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

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

Downstream raw materials:

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

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

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