4'',6''-O-benzylidene-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-5,2''-dideoxydibekacin

Base Information

Chemical Name:4'',6''-O-benzylidene-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-5,2''-dideoxydibekacin
CAS No.:161822-08-8
Molecular Formula:C₆₁H₈₆N₆O₁₈
Molecular Weight:1191.38
Hs Code.:

Synonyms:4'',6''-O-benzylidene-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-5,2''-dideoxydibekacin

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Chemical Property of 4'',6''-O-benzylidene-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-5,2''-dideoxydibekacin

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Technology Process of 4'',6''-O-benzylidene-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-5,2''-dideoxydibekacin

There total 8 articles about 4'',6''-O-benzylidene-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-5,2''-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: 92.0%

: 161822-07-7
4'',6''-O-benzylidene-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2''-deoxy-5-O-(methylthio)-thiocarbonyldibekacin

: 161822-08-8
4'',6''-O-benzylidene-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-5,2''-dideoxydibekacin

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 110 ℃; for 0.833333h;
DOI:10.7164/antibiotics.47.821

Reference yield:

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

: 161822-08-8
4'',6''-O-benzylidene-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-5,2''-dideoxydibekacin

Guidance literature:: Multi-step reaction with 7 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: 1.) 8M NaOH / 1.) DMSO, r.t., 30 min, 2.) DMSO, 2 h

7: 92 percent / Bu₃SnH, 2,2'-azobis(isobutyronitrile) / toluene / 0.83 h / 110 °C

With pyridine; sodium hydroxide; 2,2'-azobis(isobutyronitrile); ammonium acetate; tri-n-butyl-tin hydride; pyridinium trifluroacetate; oxalic acid; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;
DOI:10.7164/antibiotics.47.821

Reference yield:

: 3,2',6'-tris(N-tert-butoxycarbonyl)dibekacin

: 161822-08-8
4'',6''-O-benzylidene-1,3''-bis(N-benzyloxycarbonyl)-3,2',6'-tris(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-5,2''-dideoxydibekacin

Guidance literature:: Multi-step reaction with 7 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: 1.) 8M NaOH / 1.) DMSO, r.t., 30 min, 2.) DMSO, 2 h

7: 92 percent / Bu₃SnH, 2,2'-azobis(isobutyronitrile) / toluene / 0.83 h / 110 °C

With pyridine; sodium hydroxide; 2,2'-azobis(isobutyronitrile); ammonium acetate; tri-n-butyl-tin hydride; pyridinium trifluroacetate; oxalic acid; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;
DOI:10.7164/antibiotics.47.821