(1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-2-bromo-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>nonane

Base Information

Chemical Name:(1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-2-bromo-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>nonane
CAS No.:124287-87-2
Molecular Formula:C₂₂H₃₃BrN₂O₅Si
Molecular Weight:513.504
Hs Code.:

Synonyms:(1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-2-bromo-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>nonane

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Chemical Property of (1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-2-bromo-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>nonane

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Technology Process of (1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-2-bromo-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>nonane

There total 12 articles about (1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-2-bromo-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>nonane 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: 71.0%

: 111515-82-3
(1R,2R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>nonanecarboxylic acid

: 124287-87-2
(1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-2-bromo-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>nonane

Guidance literature:: With dmap; Bromotrichloromethane; 2-mercaptopyridine-1-oxide sodium salt; trichloromethyl chloroformate; In tetrahydrofuran; benzene; for 10h; Heating;
DOI:10.1021/jo00291a014

Reference yield:

: 111535-89-8
methyl (1R,2R,4R,5R,6S)-4,5-epoxy-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>nonanecarboxylate

: 124287-87-2
(1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-2-bromo-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>nonane

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / trimethylsilyl azide, ZnCl₂ / 1,2-dichloro-ethane / 1.5 h / Heating

2: 1) H₂ 2) aq.NaHCO₃ / 1) 10percent Pd/C / 1) MeOH, r.t., 2 h 2) r.t., 1 h

3: 92 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

4: 100 percent / 1N NaOH / methanol / 12 h / Ambient temperature

5: 71 percent / 2-mercaptopyridine N-oxide sodium salt, phosgene dimer, (dimethylamino)pyridine, BrCCl₃ / benzene; tetrahydrofuran / 10 h / Heating

With 1H-imidazole; dmap; sodium hydroxide; Bromotrichloromethane; trimethylsilylazide; hydrogen; 2-mercaptopyridine-1-oxide sodium salt; sodium hydrogencarbonate; zinc(II) chloride; trichloromethyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00291a014

Reference yield:

: 111515-80-1
methyl (1R,2R,4S,5R,6R)-4-azido-5-hydroxy-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>nonanecarboxylate

: 124287-87-2
(1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-2-bromo-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>nonane

Guidance literature:: Multi-step reaction with 4 steps

1: 1) H₂ 2) aq.NaHCO₃ / 1) 10percent Pd/C / 1) MeOH, r.t., 2 h 2) r.t., 1 h

2: 92 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

3: 100 percent / 1N NaOH / methanol / 12 h / Ambient temperature

4: 71 percent / 2-mercaptopyridine N-oxide sodium salt, phosgene dimer, (dimethylamino)pyridine, BrCCl₃ / benzene; tetrahydrofuran / 10 h / Heating

With 1H-imidazole; dmap; sodium hydroxide; Bromotrichloromethane; hydrogen; 2-mercaptopyridine-1-oxide sodium salt; sodium hydrogencarbonate; trichloromethyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00291a014