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

Base Information

• Chemical Name: 1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2''-deoxydibekacin
• CAS No.: 161822-12-4
• Molecular Formula: C₅₄H₈₂N₆O₁₉
• Molecular Weight: 1119.27

Synonyms:1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2''-deoxydibekacin

Chemical Property of 1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2''-deoxydibekacin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2''-deoxydibekacin

There total 7 articles about 1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2''-deoxydibekacin 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: 95.0%

4'',6''-O-benzylidene-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2''-deoxydibekacin (161906-84-9) → 1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2''-deoxydibekacin (161822-12-4)

Guidance literature:

With water; trifluoroacetic acid; In methanol; Ambient temperature;

DOI:10.7164/antibiotics.47.821

Reference yield:

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) → 1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2''-deoxydibekacin (161822-12-4)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; ammonium acetate; water; pyridinium trifluroacetate; oxalic acid; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.47.821

Reference yield:

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''-deoxydibekacin (161822-12-4)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; ammonium acetate; water; pyridinium trifluroacetate; oxalic acid; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.47.821

upstream raw materials:

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

N-(Benzyloxycarbonyloxy)succinimide

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

4'',6''-O-benzylidene-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)dibekacin

Downstream raw materials:

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

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

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

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

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