Benzoic acid (2S,3R,4R,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R,4R,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester
• CAS No.: 160529-98-6
• Molecular Formula: C₂₉H₂₉F₃O₉S
• Molecular Weight: 610.605
• Mol file: 160529-98-6.mol

Synonyms:Benzoic acid (2S,3R,4R,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2S,3R,4R,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,3R,4R,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester

There total 1 articles about Benzoic acid (2S,3R,4R,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester 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:

trifluoromethylsulfonic anhydride (358-23-6) + methyl 2-O-benzoyl-3,6-di-O-benzyl-α-D-glucopyranoside (160529-97-5) → Benzoic acid (2S,3R,4R,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester (160529-98-6)

Guidance literature:

With pyridine; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/0008-6215(94)84194-2

Reference yield: 88.0%

Benzoic acid (2S,3R,4R,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester (160529-98-6) → methyl 3,6-di-O-benzyl-4-deoxy-4-fluoro-α-D-galactopyranoside (160530-00-7) + methyl 2-O-benzoyl-3,6-di-O-benzyl-4-deoxy-4-fluoro-α-D-galactopyranoside

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In dichloromethane; for 40h;

DOI:10.1016/0008-6215(94)84194-2

Reference yield:

Benzoic acid (2S,3R,4R,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester (160529-98-6) → methyl O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1<*>2)-4-deoxy-4-fluoro-α-D-galactopyranoside (160530-05-2)

Guidance literature:

Multi-step reaction with 3 steps

1: TAS-F / CH₂Cl₂ / 40 h

2: 91.5 percent / sym-collidine, AgOTf / CH₂Cl₂ / 2.67 h / -20 - 20 °C

3: 92 percent / H₂ / 10percent Pd/C / acetone; ethanol

With 2,4,6-trimethyl-pyridine; hydrogen; silver trifluoromethanesulfonate; tris(dimethylamino)sulfonium trimethylsilyldifluoride; palladium on activated charcoal; In ethanol; dichloromethane; acetone;

DOI:10.1016/0008-6215(94)84194-2

upstream raw materials:

trifluoromethylsulfonic anhydride

methyl 2-O-benzoyl-3,6-di-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

methyl 3,6-di-O-benzyl-4-deoxy-4-fluoro-α-D-galactopyranoside

methyl O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1<*>2)-4-deoxy-4-fluoro-α-D-galactopyranoside

methyl O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1<*>2)-3,6-di-O-benzyl-4-deoxy-4-fluoro-α-D-galactopyranoside