3''-(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2'',4''-dideoxydibekacin

Base Information

• Chemical Name: 3''-(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2'',4''-dideoxydibekacin
• CAS No.: 161822-16-8
• Molecular Formula: C₄₆H₇₆N₆O₁₆
• Molecular Weight: 969.14
• Mol file: 161822-16-8.mol

Synonyms:

Chemical Property of 3''-(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2'',4''-dideoxydibekacin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3''-(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2'',4''-dideoxydibekacin

There total 13 articles about 3''-(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2'',4''-dideoxydibekacin 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: 58.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + 3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2'',4''-dideoxydibekacin diformate → 3''-(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2'',4''-dideoxydibekacin (161822-16-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; for 3h; -20 deg C - 0 deg C;

DOI:10.7164/antibiotics.47.821

Reference yield:

6''-O-benzoyl-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2''-deoxy-4''-O-mesyldibekacin (161822-13-5) → 3''-(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2'',4''-dideoxydibekacin (161822-16-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 58 percent / NaI / dimethylformamide / 20 h / 100 °C

2: 93 percent / Bu₃SnH, 2,2'-azobis(isobutyronitrile) / toluene / 2 h / 100 °C

3: 89 mg / 28percent MeONa / methanol / 17 h / Ambient temperature

4: 10percent Pd/C / methanol / 2 h / Ambient temperature

5: 58 percent / Et₃N / dimethylformamide; tetrahydrofuran / 3 h / -20 deg C - 0 deg C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.7164/antibiotics.47.821

Reference yield:

3,2',6'-tris(N-tert-butoxycarbonyl)dibekacin → 3''-(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2'',4''-dideoxydibekacin (161822-16-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 80 percent / pyridine / dimethylformamide / 4 h / Ambient temperature

2: 72 percent / p-toluenesulfonic acid / dimethylformamide / 1 h / 40 °C / 20 Torr

3: 1.) pyridinium trifluoroacetate, DMSO, dicyclohexylcarbodiimide, 2.) oxalic acid dihydrate / 1.) C₆H₆, r.t., overnight, 2.) C₆H₆, dioxane, r.t., 30 min

4: NH₄OAc, NaBH₃CN / methanol / Ambient temperature

5: 23 percent / Et₃N / tetrahydrofuran; methanol / Ambient temperature

6: 95 percent / 90percent CF₃COOH/H₂O / methanol / Ambient temperature

7: 89 percent / pyridine / 4 h / Ambient temperature

8: 89 percent / pyridine / 16 h / 40 °C

9: 58 percent / NaI / dimethylformamide / 20 h / 100 °C

10: 93 percent / Bu₃SnH, 2,2'-azobis(isobutyronitrile) / toluene / 2 h / 100 °C

11: 89 mg / 28percent MeONa / methanol / 17 h / Ambient temperature

12: 10percent Pd/C / methanol / 2 h / Ambient temperature

13: 58 percent / Et₃N / dimethylformamide; tetrahydrofuran / 3 h / -20 deg C - 0 deg C

With pyridine; 2,2'-azobis(isobutyronitrile); ammonium acetate; water; tri-n-butyl-tin hydride; sodium methylate; pyridinium trifluroacetate; oxalic acid; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.7164/antibiotics.47.821

upstream raw materials:

N-(Benzyloxycarbonyloxy)succinimide

6''-O-benzoyl-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2''-deoxy-4''-O-mesyldibekacin

1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)dibekacin

1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2'',4''-dideoxydibekacin

Refernces