benzyl O-<4,6-O-(4-nitrobenzylidene)-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Base Information

Chemical Name:benzyl O-<4,6-O-(4-nitrobenzylidene)-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside
CAS No.:142072-47-7
Molecular Formula:C₄₉H₅₁N₃O₁₄
Molecular Weight:905.956
Hs Code.:

benzyl O-<4,6-O-(4-nitrobenzylidene)-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

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Chemical Property of benzyl O-<4,6-O-(4-nitrobenzylidene)-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

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Technology Process of benzyl O-<4,6-O-(4-nitrobenzylidene)-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

There total 8 articles about benzyl O-<4,6-O-(4-nitrobenzylidene)-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-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:

: 34368-66-6
1,2-O-isopropylidene-3-O-phenylcarbamoyl-α-D-glucofuranose

: 142072-47-7
benzyl O-<4,6-O-(4-nitrobenzylidene)-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / 0.05 M H₂SO₄ / dioxane / 5 h / 100 °C

2: 93 percent / pyridine, 4-dimethylaminopyridine / 5 h / Ambient temperature

3: 82 percent / 33 percent HBr-AcOH / CHCl₃ / 5.5 h / Ambient temperature

4: 1.) silver triflate, molecular sieves 4 Angstroem / 1.) dichloromethane, r.t., 1 h, then -40 deg C, 2.) dichloromethane, - 10 deg C

5: K₂CO₃ / methanol / 6 h / Ambient temperature

6: 1.) 4-toluenesulfonic acid monohydrate / 1.) benzene, N,N-dimethylformamide, reflux, 15 min, 2.) heating, 3 h

With pyridine; dmap; 4 A molecular sieve; sulfuric acid; p-toluenesulfonic acid monohydrate; hydrogen bromide; silver trifluoromethanesulfonate; potassium carbonate; acetic acid; In 1,4-dioxane; methanol; chloroform;
DOI:10.1016/S0008-6215(00)90561-5

Reference yield:

: 103-71-9
phenyl isocyanate

: 142072-47-7
benzyl O-<4,6-O-(4-nitrobenzylidene)-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / 4-dimethylaminopyridine / toluene / 3 h / 100 °C

2: aq. acetic acid

3: 87 percent / 0.05 M H₂SO₄ / dioxane / 5 h / 100 °C

4: 93 percent / pyridine, 4-dimethylaminopyridine / 5 h / Ambient temperature

5: 82 percent / 33 percent HBr-AcOH / CHCl₃ / 5.5 h / Ambient temperature

6: 1.) silver triflate, molecular sieves 4 Angstroem / 1.) dichloromethane, r.t., 1 h, then -40 deg C, 2.) dichloromethane, - 10 deg C

7: K₂CO₃ / methanol / 6 h / Ambient temperature

8: 1.) 4-toluenesulfonic acid monohydrate / 1.) benzene, N,N-dimethylformamide, reflux, 15 min, 2.) heating, 3 h

With pyridine; dmap; 4 A molecular sieve; sulfuric acid; p-toluenesulfonic acid monohydrate; hydrogen bromide; silver trifluoromethanesulfonate; potassium carbonate; acetic acid; In 1,4-dioxane; methanol; chloroform; toluene;
DOI:10.1016/S0008-6215(00)90561-5

Reference yield:

: 115533-28-3
3-O-(N-phenylcarbamoyl)-D-glucopyranose

: 142072-47-7
benzyl O-<4,6-O-(4-nitrobenzylidene)-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / pyridine, 4-dimethylaminopyridine / 5 h / Ambient temperature

2: 82 percent / 33 percent HBr-AcOH / CHCl₃ / 5.5 h / Ambient temperature

3: 1.) silver triflate, molecular sieves 4 Angstroem / 1.) dichloromethane, r.t., 1 h, then -40 deg C, 2.) dichloromethane, - 10 deg C

4: K₂CO₃ / methanol / 6 h / Ambient temperature

5: 1.) 4-toluenesulfonic acid monohydrate / 1.) benzene, N,N-dimethylformamide, reflux, 15 min, 2.) heating, 3 h

With pyridine; dmap; 4 A molecular sieve; p-toluenesulfonic acid monohydrate; hydrogen bromide; silver trifluoromethanesulfonate; potassium carbonate; acetic acid; In methanol; chloroform;
DOI:10.1016/S0008-6215(00)90561-5