(3S,4R)-3-<(1R)-1-triethylsilyloxyethyl>-4-<(1R)-1-(4-tert-butoxycarbonylaminobutyl)-2-oxo-3-acetoxypropyl>-1-(diphenylmethoxycarbonyl-hydroxymethyl)-2-azetidinone

Base Information

Chemical Name:(3S,4R)-3-<(1R)-1-triethylsilyloxyethyl>-4-<(1R)-1-(4-tert-butoxycarbonylaminobutyl)-2-oxo-3-acetoxypropyl>-1-(diphenylmethoxycarbonyl-hydroxymethyl)-2-azetidinone
CAS No.:220430-29-5
Molecular Formula:C₄₀H₅₈N₂O₁₀Si
Molecular Weight:754.993
Hs Code.:

(3S,4R)-3-<(1R)-1-triethylsilyloxyethyl>-4-<(1R)-1-(4-tert-butoxycarbonylaminobutyl)-2-oxo-3-acetoxypropyl>-1-(diphenylmethoxycarbonyl-hydroxymethyl)-2-azetidinone

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Chemical Property of (3S,4R)-3-<(1R)-1-triethylsilyloxyethyl>-4-<(1R)-1-(4-tert-butoxycarbonylaminobutyl)-2-oxo-3-acetoxypropyl>-1-(diphenylmethoxycarbonyl-hydroxymethyl)-2-azetidinone

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Technology Process of (3S,4R)-3-<(1R)-1-triethylsilyloxyethyl>-4-<(1R)-1-(4-tert-butoxycarbonylaminobutyl)-2-oxo-3-acetoxypropyl>-1-(diphenylmethoxycarbonyl-hydroxymethyl)-2-azetidinone

There total 8 articles about (3S,4R)-3-<(1R)-1-triethylsilyloxyethyl>-4-<(1R)-1-(4-tert-butoxycarbonylaminobutyl)-2-oxo-3-acetoxypropyl>-1-(diphenylmethoxycarbonyl-hydroxymethyl)-2-azetidinone 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

: 220430-29-5
(3S,4R)-3-<(1R)-1-triethylsilyloxyethyl>-4-<(1R)-1-(4-tert-butoxycarbonylaminobutyl)-2-oxo-3-acetoxypropyl>-1-(diphenylmethoxycarbonyl-hydroxymethyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 3 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

With 1H-imidazole; hydrogen; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide; toluene;
DOI:10.3987/COM-98-8302

Reference yield:

: 220430-51-3
Acetic acid (S)-6-{(2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-cyclohex-1-enylmethyl ester

: 220430-29-5
(3S,4R)-3-<(1R)-1-triethylsilyloxyethyl>-4-<(1R)-1-(4-tert-butoxycarbonylaminobutyl)-2-oxo-3-acetoxypropyl>-1-(diphenylmethoxycarbonyl-hydroxymethyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 7 steps

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

2: 71 percent / NaBH₄ / CH₂Cl₂; ethanol / 0.67 h / -78 °C

3: 82 percent / triphenylphosphine, HN₃, diethyl azodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C

4: 82 percent / conc. HCl, acetic acid / acetonitrile / 2 h / 0 °C

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

6: 86 percent / H₂ / Pd/C / methanol / 0.25 h

7: 77 percent / toluene / 3 h / Heating

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

Reference yield:

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

: 220430-29-5
(3S,4R)-3-<(1R)-1-triethylsilyloxyethyl>-4-<(1R)-1-(4-tert-butoxycarbonylaminobutyl)-2-oxo-3-acetoxypropyl>-1-(diphenylmethoxycarbonyl-hydroxymethyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 8 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

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