2-azi-4-benzyloxy-1-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy)butane

Base Information

• Chemical Name: 2-azi-4-benzyloxy-1-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy)butane
• CAS No.: 186090-93-7
• Molecular Formula: C₄₅H₄₀N₂O₁₁
• Molecular Weight: 784.819
• Mol file: 186090-93-7.mol

Synonyms:2-azi-4-benzyloxy-1-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy)butane

Chemical Property of 2-azi-4-benzyloxy-1-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy)butane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azi-4-benzyloxy-1-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy)butane

There total 6 articles about 2-azi-4-benzyloxy-1-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy)butane 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:

benzyl bromide (100-39-0) → 2-azi-4-benzyloxy-1-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy)butane (186090-93-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 71 percent / NaH, Bu₄NI / dimethylformamide / 3 h / Ambient temperature

2: 92 percent / aq. acetic acid / Ambient temperature

3: 88 percent / 4-dimethylaminopyridine / pyridine / 48 h / Ambient temperature

4: 83 percent / PCC / pyridine; CH₂Cl₂ / 96 h

5: 91 percent / aq. acetic acid / 2 h / Ambient temperature

6: 1.) hydroxylamine-O-sulfonic acid, NH₃, 2.) Et₃N, I₂ / 1.) MeOH, -20 deg C, 2 h, 2.) MeOH, 0 deg C, 20 min

7: 1.) tetramethylurea, silver trifluoromethanesulfonate, 4A molecular sieves / 1.) CH₂Cl₂, rt, 1 h, 2.) CH₂Cl₂, -20 deg C, 4 h

With dmap; 4 A molecular sieve; ammonia; iodine; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; pyridinium chlorochromate; tetramethylurea; hydroxylamine-O-sulfonic acid; In pyridine; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(96)00207-8

Reference yield:

(+/-)-4-benzyloxy-butane-1,2-diol (71998-69-1) → 2-azi-4-benzyloxy-1-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy)butane (186090-93-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / 4-dimethylaminopyridine / pyridine / 48 h / Ambient temperature

2: 83 percent / PCC / pyridine; CH₂Cl₂ / 96 h

3: 91 percent / aq. acetic acid / 2 h / Ambient temperature

4: 1.) hydroxylamine-O-sulfonic acid, NH₃, 2.) Et₃N, I₂ / 1.) MeOH, -20 deg C, 2 h, 2.) MeOH, 0 deg C, 20 min

5: 1.) tetramethylurea, silver trifluoromethanesulfonate, 4A molecular sieves / 1.) CH₂Cl₂, rt, 1 h, 2.) CH₂Cl₂, -20 deg C, 4 h

With dmap; 4 A molecular sieve; ammonia; iodine; silver trifluoromethanesulfonate; triethylamine; pyridinium chlorochromate; tetramethylurea; hydroxylamine-O-sulfonic acid; In pyridine; dichloromethane; acetic acid;

DOI:10.1016/S0008-6215(96)00207-8

Reference yield:

(+/-)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane (94426-71-8) → 2-azi-4-benzyloxy-1-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy)butane (186090-93-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / aq. acetic acid / Ambient temperature

2: 88 percent / 4-dimethylaminopyridine / pyridine / 48 h / Ambient temperature

3: 83 percent / PCC / pyridine; CH₂Cl₂ / 96 h

4: 91 percent / aq. acetic acid / 2 h / Ambient temperature

5: 1.) hydroxylamine-O-sulfonic acid, NH₃, 2.) Et₃N, I₂ / 1.) MeOH, -20 deg C, 2 h, 2.) MeOH, 0 deg C, 20 min

6: 1.) tetramethylurea, silver trifluoromethanesulfonate, 4A molecular sieves / 1.) CH₂Cl₂, rt, 1 h, 2.) CH₂Cl₂, -20 deg C, 4 h

With dmap; 4 A molecular sieve; ammonia; iodine; silver trifluoromethanesulfonate; triethylamine; pyridinium chlorochromate; tetramethylurea; hydroxylamine-O-sulfonic acid; In pyridine; dichloromethane; acetic acid;

DOI:10.1016/S0008-6215(96)00207-8

upstream raw materials:

2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide

[3-(2-Benzyloxy-ethyl)-3H-diazirin-3-yl]-methanol

benzyl bromide

(+/-)-4-benzyloxy-butane-1,2-diol

Downstream raw materials:

2-azi-1-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyloxy)-5-oxa-7-thiaoctane