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

Base Information

Chemical Name:6''-O-benzoyl-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2''-deoxy-4''-O-mesyldibekacin
CAS No.:161822-13-5
Molecular Formula:C₆₂H₈₈N₆O₂₂S
Molecular Weight:1301.47
Hs Code.:

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

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

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

There total 9 articles about 6''-O-benzoyl-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2''-deoxy-4''-O-mesyldibekacin 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: 89.0%

: 124-63-0
methanesulfonyl chloride

: 1055032-19-3
6''-O-benzoyl-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2''-deoxydibekacin

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

Guidance literature:: With pyridine; at 40 ℃; for 16h;
DOI:10.7164/antibiotics.47.821

Reference yield:

: 13139-17-8
N-(Benzyloxycarbonyloxy)succinimide

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

Guidance literature:: Multi-step reaction with 8 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

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

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

Guidance literature:: Multi-step reaction with 8 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

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