(S)-4-{3-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-3-yl]-4-methoxy-benzyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-4-{3-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-3-yl]-4-methoxy-benzyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester
• CAS No.: 760979-78-0
• Molecular Formula: C₄₂H₅₈BNO₈Si
• Molecular Weight: 743.821

Synonyms:(S)-4-{3-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-3-yl]-4-methoxy-benzyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Chemical Property of (S)-4-{3-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-3-yl]-4-methoxy-benzyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

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Technology Process of (S)-4-{3-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-3-yl]-4-methoxy-benzyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

There total 10 articles about (S)-4-{3-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-3-yl]-4-methoxy-benzyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester 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: 76.0%

bis(pinacol)diborane (73183-34-3) + (S)-4-{3-[(S)-7-Bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-benzofuran-3-yl]-4-methoxy-benzyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (760980-20-9) → (S)-4-{3-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-3-yl]-4-methoxy-benzyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (760979-78-0)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In dimethyl sulfoxide; at 85 ℃; for 8h;

DOI:10.1021/ja040090y

Reference yield:

((S)-2-{3-[1-(3-Bromo-2-hydroxy-phenyl)-vinyl]-4-methoxy-phenyl}-1-hydroxymethyl-ethyl)-carbamic acid benzyl ester (760979-97-3) → (S)-4-{3-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-3-yl]-4-methoxy-benzyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (760979-78-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 95 percent / K₂CO₃ / acetone / 3 h / Heating

2.1: 86 percent / p-toluenesulfonic acid / acetone / 0.5 h / 25 °C

3.1: 97 percent / meta-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂ / 8 h / 0 °C

4.1: 52 percent / KO-t-Bu / tetrahydrofuran; dimethylformamide / 0.08 h / -78 °C

5.1: 88 percent / imidazole / dimethylformamide / 8 h / 25 °C

6.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.08 h / -78 °C

6.2: 80 percent / O₂ / tetrahydrofuran / 0.5 h / -78 °C

7.1: 96 percent / LiBH₄ / tetrahydrofuran / 8 h / 25 °C

8.1: 89 percent / 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / Heating

9.1: 76 percent / Pd(diphenylphosphinoferrocene)Cl₂*CH₂Cl₂; KOAc / dimethylsulfoxide / 8 h / 85 °C

With 1H-imidazole; lithium borohydride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium tert-butylate; potassium acetate; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; 1,1'-carbonyldiimidazole; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 9.1: Miyaura reaction;

DOI:10.1021/ja040090y

Reference yield:

(S)-4-{3-[1-(3-Bromo-2-methoxymethoxy-phenyl)-vinyl]-4-methoxy-benzyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (761433-99-2) → (S)-4-{3-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-3-yl]-4-methoxy-benzyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (760979-78-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 98 percent / aq. HCl / methanol; CH₂Cl₂ / 12 h / 25 °C

2.1: 95 percent / K₂CO₃ / acetone / 3 h / Heating

3.1: 86 percent / p-toluenesulfonic acid / acetone / 0.5 h / 25 °C

4.1: 97 percent / meta-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂ / 8 h / 0 °C

5.1: 52 percent / KO-t-Bu / tetrahydrofuran; dimethylformamide / 0.08 h / -78 °C

6.1: 88 percent / imidazole / dimethylformamide / 8 h / 25 °C

7.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.08 h / -78 °C

7.2: 80 percent / O₂ / tetrahydrofuran / 0.5 h / -78 °C

8.1: 96 percent / LiBH₄ / tetrahydrofuran / 8 h / 25 °C

9.1: 89 percent / 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / Heating

10.1: 76 percent / Pd(diphenylphosphinoferrocene)Cl₂*CH₂Cl₂; KOAc / dimethylsulfoxide / 8 h / 85 °C

With 1H-imidazole; hydrogenchloride; lithium borohydride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium tert-butylate; potassium acetate; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; 1,1'-carbonyldiimidazole; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 10.1: Miyaura reaction;

DOI:10.1021/ja040090y

upstream raw materials:

bis(pinacol)diborane

(S)-4-{3-[(S)-7-Bromo-3-(tert-butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-benzofuran-3-yl]-4-methoxy-benzyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

((S)-2-{3-[1-(3-Bromo-2-hydroxy-phenyl)-vinyl]-4-methoxy-phenyl}-1-hydroxymethyl-ethyl)-carbamic acid benzyl ester

(S)-4-{3-[1-(3-Bromo-2-methoxymethoxy-phenyl)-vinyl]-4-methoxy-benzyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Downstream raw materials:

(S)-4-[3-((S)-7-{3-[2-(Dimethoxy-phosphorylmethyl)-oxazol-5-yl]-1-methoxymethyl-1H-indol-4-yl}-3-formyl-2,3-dihydro-benzofuran-3-yl)-4-methoxy-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

[5-(4-{(R)-3-[5-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propyl)-2-methoxy-phenyl]-3-hydroxymethyl-2,3-dihydro-benzofuran-7-yl}-1-methoxymethyl-1H-indol-3-yl)-oxazol-2-ylmethyl]-phosphonic acid dimethyl ester

(S)-4-[3-((R)-7-{3-[2-(Dimethoxy-phosphorylmethyl)-oxazol-5-yl]-1-methoxymethyl-1H-indol-4-yl}-3-hydroxymethyl-2,3-dihydro-benzofuran-3-yl)-4-methoxy-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

4-[3-(3-(tert-butyl-dimethyl-silanyloxymethyl)-7-{3-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-oxazol-5-yl]-1-methoxymethyl-1H-indol-4-yl}-2,3-dihydro-benzofuran-3-yl)-4-methoxy-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

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