Trifluoro-methanesulfonic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester
• CAS No.: 59964-41-9
• Molecular Formula: C₃₅H₃₅F₃O₈S
• Molecular Weight: 672.719
• Mol file: 59964-41-9.mol

Synonyms:Trifluoro-methanesulfonic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Chemical Property of Trifluoro-methanesulfonic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Trifluoro-methanesulfonic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

There total 4 articles about Trifluoro-methanesulfonic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-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:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) + trifluoromethylsulfonic anhydride (358-23-6) → Trifluoro-methanesulfonic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (59964-41-9)

Guidance literature:

With 1,1'-sulfinylbisbenzene; In dichloromethane; toluene; at -40 ℃; for 1h;

DOI:10.1021/ja010086b

Reference yield:

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide (4196-35-4) + silver trifluoromethanesulfonate (2923-28-6) → Trifluoro-methanesulfonic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (59964-41-9)

Guidance literature:

In diethyl ether; at -35 ℃; for 0.833333h; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.carres.2011.10.002

Reference yield:

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside (38184-10-0) + trifluoromethylsulfonic anhydride (358-23-6) → Trifluoro-methanesulfonic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (59964-41-9)

Guidance literature:

With N-methylmaleimide; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -78 ℃; for 0.0833333h; Reagent/catalyst; Inert atmosphere; Molecular sieve;

DOI:10.1021/ol401095k

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

trifluoromethylsulfonic anhydride

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

silver trifluoromethanesulfonate

Downstream raw materials:

O-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl]cholesterol

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-[1:2,3:4]-di-O-isopropylidene-α-D-galactopyranoside

methyl 2-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→3)-4,6-O-benzylidene-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside