(6S)-6-O-[tert-butyl(dimethyl)silyl]-6-C-(4'-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}-3'-hydroxybiphenyl-3-yl)-1,2-O-(1-methylethylidene)-α-D-glucofuranose

Base Information

• Chemical Name: (6S)-6-O-[tert-butyl(dimethyl)silyl]-6-C-(4'-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}-3'-hydroxybiphenyl-3-yl)-1,2-O-(1-methylethylidene)-α-D-glucofuranose
• CAS No.: 852204-60-5
• Molecular Formula: C₅₁H₆₈FNO₉Si₂
• Molecular Weight: 914.272
• Mol file: 852204-60-5.mol

Synonyms:(6S)-6-O-[tert-butyl(dimethyl)silyl]-6-C-(4'-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}-3'-hydroxybiphenyl-3-yl)-1,2-O-(1-methylethylidene)-α-D-glucofuranose

Chemical Property of (6S)-6-O-[tert-butyl(dimethyl)silyl]-6-C-(4'-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}-3'-hydroxybiphenyl-3-yl)-1,2-O-(1-methylethylidene)-α-D-glucofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S)-6-O-[tert-butyl(dimethyl)silyl]-6-C-(4'-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}-3'-hydroxybiphenyl-3-yl)-1,2-O-(1-methylethylidene)-α-D-glucofuranose

There total 16 articles about (6S)-6-O-[tert-butyl(dimethyl)silyl]-6-C-(4'-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}-3'-hydroxybiphenyl-3-yl)-1,2-O-(1-methylethylidene)-α-D-glucofuranose 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:

(4S)-4-benzyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-1,3-oxazolidin-2-one (852148-48-2) → (6S)-6-O-[tert-butyl(dimethyl)silyl]-6-C-(4'-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}-3'-hydroxybiphenyl-3-yl)-1,2-O-(1-methylethylidene)-α-D-glucofuranose (852204-60-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 3,3-diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole; dimethylsulfide borane complex / dichloromethane; toluene / 5.5 h / -5 °C / Cooling with methanol-dry ice

2: 1H-imidazole / N,N-dimethyl-formamide / 19 h / 20 °C

3: N-ethyl-N,N-diisopropylamine / titanium tetrachloride / dichloromethane / 3.2 h / -30 - -25 °C

4: N,O-bis-(trimethylsilyl)-acetamide / tetrabutyl ammonium fluoride / tert-butyl methyl ether / 19 h / 20 °C

5: morpholine / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 1.5 h / 20 °C

6: 2,6-dimethylpyridine / dichloromethane; N,N-dimethyl-formamide / 6.75 h / 20 °C

7: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 24 h / 85 °C

8: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / ethanol; water; toluene / 1 h / 85 °C

With morpholine; 1H-imidazole; 2,6-dimethylpyridine; N,O-bis-(trimethylsilyl)-acetamide; 3,3-diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole; dimethylsulfide borane complex; potassium acetate; potassium carbonate; N-ethyl-N,N-diisopropylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; titanium tetrachloride; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; tert-butyl methyl ether; water; N,N-dimethyl-formamide; toluene;

Reference yield:

2-(allyloxy)-4-bromobenzaldehyde (852204-14-9) → (6S)-6-O-[tert-butyl(dimethyl)silyl]-6-C-(4'-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}-3'-hydroxybiphenyl-3-yl)-1,2-O-(1-methylethylidene)-α-D-glucofuranose (852204-60-5)

Guidance literature:

Multi-step reaction with 7 steps

1: isopropyl alcohol / 16.5 h / 50 °C

2: N-ethyl-N,N-diisopropylamine / titanium tetrachloride / dichloromethane / 3.2 h / -30 - -25 °C

3: N,O-bis-(trimethylsilyl)-acetamide / tetrabutyl ammonium fluoride / tert-butyl methyl ether / 19 h / 20 °C

4: morpholine / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 1.5 h / 20 °C

5: 2,6-dimethylpyridine / dichloromethane; N,N-dimethyl-formamide / 6.75 h / 20 °C

6: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 24 h / 85 °C

7: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / ethanol; water; toluene / 1 h / 85 °C

With morpholine; 2,6-dimethylpyridine; N,O-bis-(trimethylsilyl)-acetamide; potassium acetate; potassium carbonate; N-ethyl-N,N-diisopropylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; titanium tetrachloride; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; tert-butyl methyl ether; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

Reference yield:

(2S/2R,3S,4S,6R,7R,8S)-3-O-tert-butyldimethylsilyl-2,3,6,7-tetrahydroxy-6,7-O-isopropylidene-1,5-dioxa-2-(3-bromophenyl)-bicyclo[3.3.0]octane (852204-54-7) → (6S)-6-O-[tert-butyl(dimethyl)silyl]-6-C-(4'-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}-3'-hydroxybiphenyl-3-yl)-1,2-O-(1-methylethylidene)-α-D-glucofuranose (852204-60-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / ethanol / 1 h / 20 °C

2: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / ethanol; water; toluene / 1 h / 85 °C

With sodium tetrahydroborate; potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; water; toluene;

upstream raw materials:

(4S)-4-benzyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-1,3-oxazolidin-2-one

2-(allyloxy)-4-bromobenzaldehyde

N-{(1E)-[2-(allyloxy)-4-bromophenyl]methylene}aniline

(4S)-4-benzyl-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-1,3-oxazolidin-2-one