benzhydryl (1S,5R,6S)-1-(4-tert-butoxycarbonylaminobutyl)-2-hydroxymethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

Base Information

Chemical Name:benzhydryl (1S,5R,6S)-1-(4-tert-butoxycarbonylaminobutyl)-2-hydroxymethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate
CAS No.:220430-31-9
Molecular Formula:C₃₈H₅₄N₂O₇Si
Molecular Weight:678.941
Hs Code.:

Synonyms:benzhydryl (1S,5R,6S)-1-(4-tert-butoxycarbonylaminobutyl)-2-hydroxymethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

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Chemical Property of benzhydryl (1S,5R,6S)-1-(4-tert-butoxycarbonylaminobutyl)-2-hydroxymethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

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Technology Process of benzhydryl (1S,5R,6S)-1-(4-tert-butoxycarbonylaminobutyl)-2-hydroxymethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

There total 13 articles about benzhydryl (1S,5R,6S)-1-(4-tert-butoxycarbonylaminobutyl)-2-hydroxymethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate 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:

: 220430-50-2
Acetic acid (R)-7-azido-3-[(2R,3S)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-2-yl]-2-oxo-heptyl ester

: 220430-31-9
benzhydryl (1S,5R,6S)-1-(4-tert-butoxycarbonylaminobutyl)-2-hydroxymethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: imidazole / dimethylformamide / 0.5 h / 0 °C

2: 86 percent / H₂ / Pd/C / methanol / 0.25 h

3: 77 percent / toluene / 3 h / Heating

4: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.5 h / -40 °C

5: 2,6-lutidine, NaBr / tetrahydrofuran / 4 h / Ambient temperature

6: 57 percent / NaOMe / methanol / 5 h / 0 °C

7: toluene / 3 h / Heating

With 1H-imidazole; 2,6-dimethylpyridine; thionyl chloride; hydrogen; sodium methylate; sodium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;
DOI:10.3987/COM-98-8302

Reference yield:

: 220430-23-9
(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1S)-2-hydroxymethylcyclohex-2-enyl>-2-azetidinone

: 220430-31-9
benzhydryl (1S,5R,6S)-1-(4-tert-butoxycarbonylaminobutyl)-2-hydroxymethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 12 steps

1: triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

2: 1.) O₃; 2.) dimethyl sulfide / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 30 min

3: 71 percent / NaBH₄ / CH₂Cl₂; ethanol / 0.67 h / -78 °C

4: 82 percent / triphenylphosphine, HN₃, diethyl azodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C

5: 82 percent / conc. HCl, acetic acid / acetonitrile / 2 h / 0 °C

6: imidazole / dimethylformamide / 0.5 h / 0 °C

7: 86 percent / H₂ / Pd/C / methanol / 0.25 h

8: 77 percent / toluene / 3 h / Heating

9: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.5 h / -40 °C

10: 2,6-lutidine, NaBr / tetrahydrofuran / 4 h / Ambient temperature

11: 57 percent / NaOMe / methanol / 5 h / 0 °C

12: toluene / 3 h / Heating

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; thionyl chloride; dimethylsulfide; tris-(2-chloro-ethyl)-amine; hydrogen; sodium methylate; ozone; acetic acid; triethylamine; triphenylphosphine; sodium bromide; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.3987/COM-98-8302

Reference yield:

: 220430-44-4
(S)-6-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-cyclohex-1-enecarboxylic acid ethyl ester

: 220430-31-9
benzhydryl (1S,5R,6S)-1-(4-tert-butoxycarbonylaminobutyl)-2-hydroxymethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 13 steps

1: 60 percent / DIBAL-H / toluene; methanol / -78 - 0 °C

2: triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

3: 1.) O₃; 2.) dimethyl sulfide / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 30 min

4: 71 percent / NaBH₄ / CH₂Cl₂; ethanol / 0.67 h / -78 °C

5: 82 percent / triphenylphosphine, HN₃, diethyl azodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C

6: 82 percent / conc. HCl, acetic acid / acetonitrile / 2 h / 0 °C

7: imidazole / dimethylformamide / 0.5 h / 0 °C

8: 86 percent / H₂ / Pd/C / methanol / 0.25 h

9: 77 percent / toluene / 3 h / Heating

10: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.5 h / -40 °C

11: 2,6-lutidine, NaBr / tetrahydrofuran / 4 h / Ambient temperature

12: 57 percent / NaOMe / methanol / 5 h / 0 °C

13: toluene / 3 h / Heating

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; thionyl chloride; dimethylsulfide; tris-(2-chloro-ethyl)-amine; hydrogen; sodium methylate; diisobutylaluminium hydride; ozone; acetic acid; triethylamine; triphenylphosphine; sodium bromide; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.3987/COM-98-8302