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

Base Information

• Chemical Name: 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl N-phenyltrifluoroacetimidate
• CAS No.: 1371597-38-4
• Molecular Formula: C₄₂H₄₀F₃NO₆
• Molecular Weight: 711.778

Synonyms:2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl N-phenyltrifluoroacetimidate

Chemical Property of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl N-phenyltrifluoroacetimidate

Chemical Property:

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Technology Process of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl N-phenyltrifluoroacetimidate

There total 4 articles about 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl N-phenyltrifluoroacetimidate 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: 95.0%

2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3) + 2,2,2-trifluoro-N-phenyl-acetimidoyl chloride (61881-19-4) → 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl N-phenyltrifluoroacetimidate (1371597-38-4)

Guidance literature:

With potassium carbonate; In acetone; for 3h; Inert atmosphere;

DOI:10.1039/d0ob01776k

Reference yield: 36.0%

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) + 2,2,2-trifluoro-N-phenyl-acetimidoyl chloride (61881-19-4) → 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl N-phenyltrifluoroacetimidate (1371597-38-4)

Guidance literature:

With potassium carbonate; In acetone; at 40 ℃; for 1.5h;

DOI:10.1002/ejoc.201700671

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) + 2,2,2-trifluoro-N-phenyl-acetimidoyl chloride (61881-19-4) → N-phenyl-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl) trifluoroacetimidate (1228757-57-0) + 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl N-phenyltrifluoroacetimidate (1371597-38-4)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 3h; Overall yield = 72 %; Inert atmosphere;

DOI:10.1021/ja411746a

upstream raw materials:

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

2,2,2-trifluoro-N-phenyl-acetimidoyl chloride

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside

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

Downstream raw materials:

allyl 3-O-acetyl-2-deoxy-2-(2,2,2-trichloroethyloxycarbonyl)-amino-4,6-O-(di-tertbutylsilanediyl)-α-D-galactosamine-(1→2)-4,6-di-O-benzylidene-3-O-[2,3,4,6-tetra-O-benzyl-α-D-glycopyranosyl]-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-O-levulinoyl-α-D-mannopyranoside

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

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

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