methyl 2-O-trifluoromethanesulfonyl-3-O-benzyl-(R)-4,6-O-benzylidene-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-O-trifluoromethanesulfonyl-3-O-benzyl-(R)-4,6-O-benzylidene-α-D-glucopyranoside
• CAS No.: 94160-77-7
• Molecular Formula: C₂₂H₂₃F₃O₈S
• Molecular Weight: 504.481
• Mol file: 94160-77-7.mol

Synonyms:methyl 2-O-trifluoromethanesulfonyl-3-O-benzyl-(R)-4,6-O-benzylidene-α-D-glucopyranoside

Chemical Property of methyl 2-O-trifluoromethanesulfonyl-3-O-benzyl-(R)-4,6-O-benzylidene-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-trifluoromethanesulfonyl-3-O-benzyl-(R)-4,6-O-benzylidene-α-D-glucopyranoside

There total 3 articles about methyl 2-O-trifluoromethanesulfonyl-3-O-benzyl-(R)-4,6-O-benzylidene-α-D-glucopyranoside 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: 99.0%

trifluoromethylsulfonic anhydride (358-23-6) + methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside (76419-48-2) → methyl 2-O-trifluoromethanesulfonyl-3-O-benzyl-(R)-4,6-O-benzylidene-α-D-glucopyranoside (94160-77-7)

Guidance literature:

With pyridine; In dichloromethane; at -15 ℃; for 2.5h; Inert atmosphere;

DOI:10.1016/j.carres.2017.09.015

Reference yield: 26.0%

C22H23F3O8S → methyl 3-O-benzyl-4,6-O-benzylidene-2-fluoro-2-deoxy-β-D-mannopyranoside + methyl 2-O-trifluoromethanesulfonyl-3-O-benzyl-(R)-4,6-O-benzylidene-α-D-glucopyranoside (94160-77-7) + 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-mannopyranosyl fluoride

Guidance literature:

With triethylamine tris(hydrogen fluoride); In ethyl acetate; at 20 ℃; for 48h;

DOI:10.1055/s-0036-1588624

Reference yield:

1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose (591727-19-4) → methyl 2-O-trifluoromethanesulfonyl-3-O-benzyl-(R)-4,6-O-benzylidene-α-D-glucopyranoside (94160-77-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 5percent HCl 2.) ZnCl₂ / 1.) MeOH

2: pyridine / CH₂Cl₂ / -15 °C

With pyridine; hydrogenchloride; zinc(II) chloride; In dichloromethane;

DOI:10.1016/0040-4039(84)80058-1

upstream raw materials:

trifluoromethylsulfonic anhydride

methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside

1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose

Downstream raw materials:

methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside

(2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

methyl 3-O-benzyl-2,4-dideoxy-2,4-difluoro-6-O-pivaloyl-α-D-talopyranoside

methyl 3-O-benzyl-2-deoxy-2-fluoro-6-O-pivaloyl-4-O-trifluoromethanesulfonyl-α-D-mannopyranoside