benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-β-D-glucopyranoside
• CAS No.: 119324-38-8
• Molecular Formula: C₂₅H₂₇N₃O₁₂
• Molecular Weight: 561.502
• Mol file: 119324-38-8.mol

Synonyms:benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-β-D-glucopyranoside

Chemical Property of benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-β-D-glucopyranoside

There total 8 articles about benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-β-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:

3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-α-D-glucopyranosyl trichloroacetimidate + benzyl alcohol (100-51-6,185532-71-2) → benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-β-D-glucopyranoside (119324-38-8) + benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-α-D-glucopyranoside (104243-12-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at -20 ℃; for 2h; Overall yield = 95 %; Overall yield = 19 mg; diastereoselective reaction; Molecular sieve;

DOI:10.1016/j.tetlet.2017.06.037

Reference yield:

C20H22Cl3N3O10 + benzyl alcohol (100-51-6,185532-71-2) → benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-β-D-glucopyranoside (119324-38-8) + benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-α-D-glucopyranoside (104243-12-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at -20 ℃; for 2h; Overall yield = 100 %; Overall yield = 20.6 mg; diastereoselective reaction; Molecular sieve;

DOI:10.1016/j.tetlet.2017.06.037

Reference yield:

2,4-Dinitrofluorobenzene (70-34-8,65727-75-5) → benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-β-D-glucopyranoside (119324-38-8) + benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-α-D-glucopyranoside (104243-12-1)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / water; N,N-dimethyl-formamide / 2 h / 20 °C

2: pyridine / 1 h / 20 °C

3: hydrazinium monoacetate / N,N-dimethyl-formamide / 2 h / 20 °C

4: caesium carbonate / dichloromethane / 1 h / 20 °C

5: trimethylsilyl trifluoromethanesulfonate / diethyl ether / 2 h / -20 °C / Molecular sieve

With pyridine; trimethylsilyl trifluoromethanesulfonate; hydrazinium monoacetate; caesium carbonate; triethylamine; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2017.06.037

upstream raw materials:

(+)-D-glucosamine hydrochloride

2,4-Dinitrofluorobenzene

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-α-D-glucopyranose

2-deoxy-2-(2,4-dinitro-phenyl)amino-D-glucose