3-[1-(2-benzyloxy-3,5-dimethoxy-4-methylphenyl)-2-(tert-butyldiphenylsilanyloxy)ethyl]-4-hydroxymethyl-6-methylene-2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Base Information

Chemical Name:3-[1-(2-benzyloxy-3,5-dimethoxy-4-methylphenyl)-2-(tert-butyldiphenylsilanyloxy)ethyl]-4-hydroxymethyl-6-methylene-2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester
CAS No.:767344-15-0
Molecular Formula:C₄₇H₅₈N₂O₈Si
Molecular Weight:807.072
Hs Code.:

3-[1-(2-benzyloxy-3,5-dimethoxy-4-methylphenyl)-2-(tert-butyldiphenylsilanyloxy)ethyl]-4-hydroxymethyl-6-methylene-2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Synonyms:3-[1-(2-benzyloxy-3,5-dimethoxy-4-methylphenyl)-2-(tert-butyldiphenylsilanyloxy)ethyl]-4-hydroxymethyl-6-methylene-2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

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Chemical Property of 3-[1-(2-benzyloxy-3,5-dimethoxy-4-methylphenyl)-2-(tert-butyldiphenylsilanyloxy)ethyl]-4-hydroxymethyl-6-methylene-2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

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Technology Process of 3-[1-(2-benzyloxy-3,5-dimethoxy-4-methylphenyl)-2-(tert-butyldiphenylsilanyloxy)ethyl]-4-hydroxymethyl-6-methylene-2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

There total 15 articles about 3-[1-(2-benzyloxy-3,5-dimethoxy-4-methylphenyl)-2-(tert-butyldiphenylsilanyloxy)ethyl]-4-hydroxymethyl-6-methylene-2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl 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:

: 19676-67-6
2,4-dimethoxy-3-methylphenol

: 767344-15-0
3-[1-(2-benzyloxy-3,5-dimethoxy-4-methylphenyl)-2-(tert-butyldiphenylsilanyloxy)ethyl]-4-hydroxymethyl-6-methylene-2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: 85 percent / CF₃CO₂H / CH₂Cl₂ / 2 h / -10 °C

2.1: 98 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

3.1: 100 percent / NaBH₄ / methanol; CH₂Cl₂ / 1.5 h / 0 °C

4.1: 93 percent / imidazole / dimethylformamide / 1 h / 20 °C

5.1: Pb(OAc)4 / acetonitrile / 0.5 h / 0 °C

6.1: 6.36 g / NH₂OH*H₂O; NaOAc / ethanol / 1.5 h / 20 °C

7.1: 95 percent / methanol / 0.5 h / 20 °C

8.1: CF₃CO₂H / CH₂Cl₂ / 0 - 20 °C

8.2: 87 percent / toluene / 1 h / Heating

9.1: 92 percent / 4-dimethylaminopyridine / acetonitrile / 6.5 h / 20 °C

10.1: NaBH₄; H₂SO₄ / ethanol; CH₂Cl₂ / 0 °C

11.1: 1.69 g / camphorsulfonic acid; quinoline / toluene / 2 h / Heating

12.1: 53 percent / Et₃N / Pd₂(dba)3 / N,N-dimethyl-acetamide / 38 h / 80 °C

13.1: dimethyldioxirane; Na₂SO₄ / acetone; methanol / 0.5 h / 0 °C

13.2: 100 percent / camphorsulfonic acid / acetone / 0 - 20 °C

14.1: 79 percent / NaBH₃CN; HCO₂H / CH₂Cl₂ / 5 h / 0 °C

15.1: TMSOK / acetonitrile / 0.5 h / 0 °C

16.1: 65 mg / K₂CO₃ / dimethylformamide / 3 h / 20 °C

With 1H-imidazole; quinoline; lead(IV) acetate; dmap; sodium tetrahydroborate; formic acid; sulfuric acid; camphor-10-sulfonic acid; potassium trimethylsilonate; hydroxylamine; sodium acetate; 3,3-dimethyldioxirane; sodium cyanoborohydride; potassium carbonate; sodium sulfate; triethylamine; trifluoroacetic acid; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In methanol; ethanol; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 7.1: Ugi reaction / 12.1: Mizoroki-Heck reaction;
DOI:10.1021/ol048857e

Reference yield:

: 360778-77-4
3-(2-hydroxy-3,5-dimethoxy-4-methylphenyl)-6,6-dimethyl-5-phenylmorpholin-2-one

: 767344-15-0
3-[1-(2-benzyloxy-3,5-dimethoxy-4-methylphenyl)-2-(tert-butyldiphenylsilanyloxy)ethyl]-4-hydroxymethyl-6-methylene-2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: 98 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

2.1: 100 percent / NaBH₄ / methanol; CH₂Cl₂ / 1.5 h / 0 °C

3.1: 93 percent / imidazole / dimethylformamide / 1 h / 20 °C

4.1: Pb(OAc)4 / acetonitrile / 0.5 h / 0 °C

5.1: 6.36 g / NH₂OH*H₂O; NaOAc / ethanol / 1.5 h / 20 °C

6.1: 95 percent / methanol / 0.5 h / 20 °C

7.1: CF₃CO₂H / CH₂Cl₂ / 0 - 20 °C

7.2: 87 percent / toluene / 1 h / Heating

8.1: 92 percent / 4-dimethylaminopyridine / acetonitrile / 6.5 h / 20 °C

9.1: NaBH₄; H₂SO₄ / ethanol; CH₂Cl₂ / 0 °C

10.1: 1.69 g / camphorsulfonic acid; quinoline / toluene / 2 h / Heating

11.1: 53 percent / Et₃N / Pd₂(dba)3 / N,N-dimethyl-acetamide / 38 h / 80 °C

12.1: dimethyldioxirane; Na₂SO₄ / acetone; methanol / 0.5 h / 0 °C

12.2: 100 percent / camphorsulfonic acid / acetone / 0 - 20 °C

13.1: 79 percent / NaBH₃CN; HCO₂H / CH₂Cl₂ / 5 h / 0 °C

14.1: TMSOK / acetonitrile / 0.5 h / 0 °C

15.1: 65 mg / K₂CO₃ / dimethylformamide / 3 h / 20 °C

With 1H-imidazole; quinoline; lead(IV) acetate; dmap; sodium tetrahydroborate; formic acid; sulfuric acid; camphor-10-sulfonic acid; potassium trimethylsilonate; hydroxylamine; sodium acetate; 3,3-dimethyldioxirane; sodium cyanoborohydride; potassium carbonate; sodium sulfate; triethylamine; trifluoroacetic acid; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In methanol; ethanol; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 6.1: Ugi reaction / 11.1: Mizoroki-Heck reaction;
DOI:10.1021/ol048857e

Reference yield:

: 360778-80-9
methanesulfonic acid 6-(6,6-dimethyl-2-oxo-5-phenylmorpholin-3-yl)-2,4-dimethoxy-3-methylphenyl ester

: 767344-15-0
3-[1-(2-benzyloxy-3,5-dimethoxy-4-methylphenyl)-2-(tert-butyldiphenylsilanyloxy)ethyl]-4-hydroxymethyl-6-methylene-2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 100 percent / NaBH₄ / methanol; CH₂Cl₂ / 1.5 h / 0 °C

2.1: 93 percent / imidazole / dimethylformamide / 1 h / 20 °C

3.1: Pb(OAc)4 / acetonitrile / 0.5 h / 0 °C

4.1: 6.36 g / NH₂OH*H₂O; NaOAc / ethanol / 1.5 h / 20 °C

5.1: 95 percent / methanol / 0.5 h / 20 °C

6.1: CF₃CO₂H / CH₂Cl₂ / 0 - 20 °C

6.2: 87 percent / toluene / 1 h / Heating

7.1: 92 percent / 4-dimethylaminopyridine / acetonitrile / 6.5 h / 20 °C

8.1: NaBH₄; H₂SO₄ / ethanol; CH₂Cl₂ / 0 °C

9.1: 1.69 g / camphorsulfonic acid; quinoline / toluene / 2 h / Heating

10.1: 53 percent / Et₃N / Pd₂(dba)3 / N,N-dimethyl-acetamide / 38 h / 80 °C

11.1: dimethyldioxirane; Na₂SO₄ / acetone; methanol / 0.5 h / 0 °C

11.2: 100 percent / camphorsulfonic acid / acetone / 0 - 20 °C

12.1: 79 percent / NaBH₃CN; HCO₂H / CH₂Cl₂ / 5 h / 0 °C

13.1: TMSOK / acetonitrile / 0.5 h / 0 °C

14.1: 65 mg / K₂CO₃ / dimethylformamide / 3 h / 20 °C

With 1H-imidazole; quinoline; lead(IV) acetate; dmap; sodium tetrahydroborate; formic acid; sulfuric acid; camphor-10-sulfonic acid; potassium trimethylsilonate; hydroxylamine; sodium acetate; 3,3-dimethyldioxirane; sodium cyanoborohydride; potassium carbonate; sodium sulfate; triethylamine; trifluoroacetic acid; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In methanol; ethanol; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 5.1: Ugi reaction / 10.1: Mizoroki-Heck reaction;
DOI:10.1021/ol048857e