N-benzyloxycarbonyl-3,4-di-O-benzyl-2,6-di-O-benzoyl-1,5-dideoxy-1,5-imino-D-mannitol

Base Information

• Chemical Name: N-benzyloxycarbonyl-3,4-di-O-benzyl-2,6-di-O-benzoyl-1,5-dideoxy-1,5-imino-D-mannitol
• CAS No.: 176167-00-3
• Molecular Formula: C₄₂H₃₉NO₈
• Molecular Weight: 685.774
• Mol file: 176167-00-3.mol

Synonyms:N-benzyloxycarbonyl-3,4-di-O-benzyl-2,6-di-O-benzoyl-1,5-dideoxy-1,5-imino-D-mannitol

Chemical Property of N-benzyloxycarbonyl-3,4-di-O-benzyl-2,6-di-O-benzoyl-1,5-dideoxy-1,5-imino-D-mannitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyloxycarbonyl-3,4-di-O-benzyl-2,6-di-O-benzoyl-1,5-dideoxy-1,5-imino-D-mannitol

There total 12 articles about N-benzyloxycarbonyl-3,4-di-O-benzyl-2,6-di-O-benzoyl-1,5-dideoxy-1,5-imino-D-mannitol 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: 91.0%

benzoic acid (65-85-0,8013-63-6) + N-benzyloxycarbonyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol (176483-87-7) → N-benzyloxycarbonyl-3,4-di-O-benzyl-2,6-di-O-benzoyl-1,5-dideoxy-1,5-imino-D-mannitol (176167-00-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/0040-4039(96)00096-2

Reference yield:

N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol (157363-86-5) → N-benzyloxycarbonyl-3,4-di-O-benzyl-2,6-di-O-benzoyl-1,5-dideoxy-1,5-imino-D-mannitol (176167-00-3)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 20percent Pd(OH)2/C / ethanol / 2.5 h

2: 90 percent / K₂CO₃ / dimethylformamide / 0.5 h / 0 °C

3: 91 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 15 h / 0 °C

With hydrogen; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(96)00266-0

Reference yield:

N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-2,6-di-O-methanesulfonyl-D-glucitol (176300-11-1) → N-benzyloxycarbonyl-3,4-di-O-benzyl-2,6-di-O-benzoyl-1,5-dideoxy-1,5-imino-D-mannitol (176167-00-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 31 percent / dimethylformamide / 24 h / 35 °C

2: K₂CO₃, MeOH / 0.5 h / 20 °C

3: H₂ / 20percent Pd(OH)2/C / ethanol / 2.5 h

4: 90 percent / K₂CO₃ / dimethylformamide / 0.5 h / 0 °C

5: 91 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 15 h / 0 °C

With methanol; hydrogen; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(96)00266-0

upstream raw materials:

benzoic acid

N-benzyloxycarbonyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol

benzyl chloroformate

(2R,3R,4R,5R)-3,4-Bis-benzyloxy-1,6-bis-(tert-butyl-dimethyl-silanyloxy)-hexane-2,5-diol

Downstream raw materials:

1-deoxymannojirimycin

3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol