2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate

Base Information

• Chemical Name: 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate
• CAS No.: 339276-14-1
• Molecular Formula: C₄₂H₄₀F₃NO₆
• Molecular Weight: 711.778
• Mol file: 339276-14-1.mol

Synonyms:2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate

Chemical Property of 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate

There total 1 articles about 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 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: 92.0%

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-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate (339276-14-1)

Guidance literature:

With potassium carbonate; 1-amino-3-(dimethylamino)propane; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/acs.orglett.5b00041

Reference yield: 99.0%

methyl 2,3,4-tri-O-benzyl-6-O-(trimethylsilyl)-α-D-glucopyranoside (78687-40-8) + 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate (339276-14-1) → methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside (56632-57-6,61474-61-1,108739-68-0,108739-69-1,117894-96-9,117894-97-0,123806-49-5,123806-50-8,129832-16-2,130794-95-5,139403-38-6,144069-05-6,144069-06-7,151379-73-6,151379-74-7,55094-26-3)

Guidance literature:

With trimethylsilyl iodide; Triphenylphosphine oxide; In dichloromethane; at 18 ℃; for 48h; stereoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.1c02947

Reference yield: 97.0%

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) + 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate (339276-14-1) → (3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-5-((((3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran (173395-55-6)

Guidance literature:

With bismuth(lll) trifluoromethanesulfonate; 4 A molecular sieve; In 1,4-dioxane; 1,2-dimethoxyethane; toluene; at -70 - -50 ℃;

DOI:10.1016/j.tetlet.2006.02.034

upstream raw materials:

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

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

Downstream raw materials:

(3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-5-((((3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran

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

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