2,2,2-Trifluoro-ethanesulfonic acid (2R,3S,4S,5R,6R)-4-allyloxy-6-allyloxymethyl-5-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-yl ester

Base Information

• Chemical Name: 2,2,2-Trifluoro-ethanesulfonic acid (2R,3S,4S,5R,6R)-4-allyloxy-6-allyloxymethyl-5-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-yl ester
• CAS No.: 105265-59-6
• Molecular Formula: C₂₂H₂₉F₃O₁₀S₂
• Molecular Weight: 574.593
• Mol file: 105265-59-6.mol

Synonyms:

Chemical Property of 2,2,2-Trifluoro-ethanesulfonic acid (2R,3S,4S,5R,6R)-4-allyloxy-6-allyloxymethyl-5-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2,2-Trifluoro-ethanesulfonic acid (2R,3S,4S,5R,6R)-4-allyloxy-6-allyloxymethyl-5-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-yl ester

There total 3 articles about 2,2,2-Trifluoro-ethanesulfonic acid (2R,3S,4S,5R,6R)-4-allyloxy-6-allyloxymethyl-5-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-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:

((3aS,5R,6R,7S,7aS)-7-Allyloxy-5-allyloxymethyl-6-benzyloxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-2-yl)-methanol → 2,2,2-Trifluoro-ethanesulfonic acid (2R,3S,4S,5R,6R)-4-allyloxy-6-allyloxymethyl-5-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-yl ester (105265-59-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) sodium methoxyde / 1.) glacial AcOH-H₂O, heated, 1 h; 2.) methanol, 5 deg C

2: 68 percent / CH₂Cl₂ / 0 deg C, 0.5 h then roomtemp., 3 h

3: acetonitrile / 1 h

With sodium methylate; In dichloromethane; acetonitrile;

DOI:10.1246/bcsj.59.1581

Reference yield:

3,6-di-O-allyl-4-O-benzyl-2-O-mesyl-α-D-mannopyranose (105265-58-5) → 2,2,2-Trifluoro-ethanesulfonic acid (2R,3S,4S,5R,6R)-4-allyloxy-6-allyloxymethyl-5-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-yl ester (105265-59-6)

Guidance literature:

In acetonitrile; for 1h;

DOI:10.1246/bcsj.59.1581

Reference yield:

3,6-di-O-allyl-4-O-benzyl-D-mannopyranose → 2,2,2-Trifluoro-ethanesulfonic acid (2R,3S,4S,5R,6R)-4-allyloxy-6-allyloxymethyl-5-benzyloxy-3-methanesulfonyloxy-tetrahydro-pyran-2-yl ester (105265-59-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / CH₂Cl₂ / 0 deg C, 0.5 h then roomtemp., 3 h

2: acetonitrile / 1 h

In dichloromethane; acetonitrile;

DOI:10.1246/bcsj.59.1581

upstream raw materials:

3,6-di-O-allyl-4-O-benzyl-2-O-mesyl-α-D-mannopyranose

Downstream raw materials:

2-<4-(p-toluenesulfonamide)phenyl>ethyl 4-O-benzyl-2-O-mesyl-β-D-mannopyranose

2-<4-(p-toluenesulfonamide)phenyl>ethyl 3,6-di-O-allyl-4-O-benzyl-2-O-mesyl-β-D-mannopyranose