4-(3-{1'-benzyl-3'-formyl-3-[2-(methoxyimino-methyl)-oxazol-5-yl]-1-methoxymethyl-2',3'-dihydro-1H,1'H-[4,7']biindolyl-3'-yl}-4-benzyloxy-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

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Chemical Name:4-(3-{1'-benzyl-3'-formyl-3-[2-(methoxyimino-methyl)-oxazol-5-yl]-1-methoxymethyl-2',3'-dihydro-1H,1'H-[4,7']biindolyl-3'-yl}-4-benzyloxy-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester
CAS No.:570377-00-3
Molecular Formula:C₅₈H₅₅N₅O₈
Molecular Weight:950.103
Hs Code.:

4-(3-{1'-benzyl-3'-formyl-3-[2-(methoxyimino-methyl)-oxazol-5-yl]-1-methoxymethyl-2',3'-dihydro-1<i>H</i>,1'<i>H</i>-[4,7']biindolyl-3'-yl}-4-benzyloxy-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Synonyms:4-(3-{1'-benzyl-3'-formyl-3-[2-(methoxyimino-methyl)-oxazol-5-yl]-1-methoxymethyl-2',3'-dihydro-1H,1'H-[4,7']biindolyl-3'-yl}-4-benzyloxy-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

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Chemical Property of 4-(3-{1'-benzyl-3'-formyl-3-[2-(methoxyimino-methyl)-oxazol-5-yl]-1-methoxymethyl-2',3'-dihydro-1H,1'H-[4,7']biindolyl-3'-yl}-4-benzyloxy-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

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Technology Process of 4-(3-{1'-benzyl-3'-formyl-3-[2-(methoxyimino-methyl)-oxazol-5-yl]-1-methoxymethyl-2',3'-dihydro-1H,1'H-[4,7']biindolyl-3'-yl}-4-benzyloxy-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

There total 17 articles about 4-(3-{1'-benzyl-3'-formyl-3-[2-(methoxyimino-methyl)-oxazol-5-yl]-1-methoxymethyl-2',3'-dihydro-1H,1'H-[4,7']biindolyl-3'-yl}-4-benzyloxy-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:

: 100-39-0
benzyl bromide

: 570377-00-3
4-(3-{1'-benzyl-3'-formyl-3-[2-(methoxyimino-methyl)-oxazol-5-yl]-1-methoxymethyl-2',3'-dihydro-1H,1'H-[4,7']biindolyl-3'-yl}-4-benzyloxy-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / KF*alumina / 1,2-dimethoxy-ethane / 12 h / 25 °C

2: 72 percent / 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 36 h / 65 °C

3: 78 mol / Pd(dppf)Cl₂*CH₂Cl₂; K₂CO₃ / 1,2-dimethoxy-ethane / 12 h / Heating

4: 94 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2.33 h / 25 - 45 °C

5: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 2 h / 0 °C

6: 0.895 g / dimethylsulfoxide / 0.25 h / 25 °C

With potassium fluoride on basic alumina; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; potassium carbonate; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; dimethyl sulfoxide; 3: Suzuki coupling;
DOI:10.1021/ja040093a

Reference yield:

: 3417-91-2
L-tyrosine methyl ester HCl

: 570377-00-3
4-(3-{1'-benzyl-3'-formyl-3-[2-(methoxyimino-methyl)-oxazol-5-yl]-1-methoxymethyl-2',3'-dihydro-1H,1'H-[4,7']biindolyl-3'-yl}-4-benzyloxy-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 16 steps

1: aq. Na₂CO₃ / CHCl₃ / 3 h / 25 °C

2: 21.8 g / TiCl₄ / CH₂Cl₂ / 6 h / 25 °C

3: SOCl₂ / 10 h / 25 °C

4: 15.7 g / NaCNBH₃ / acetonitrile / 5 h / 25 °C

5: 97 percent / LiBH₄ / tetrahydrofuran / 2 h / 25 °C

6: 98 percent / p-TsOH / acetone / 2 h / 25 °C

7: Et₃N / CH₂Cl₂ / 2 h / 0 °C

8: 7.38 g / aq. Yb(OTf)3 / tetrahydrofuran / 24 h / 25 °C

9: 84 percent / imidazole / CH₂Cl₂ / 6 h / 25 °C

10: 80 percent / LiOH / dimethylformamide / 5 h / 25 °C

11: 85 percent / KF*alumina / 1,2-dimethoxy-ethane / 12 h / 25 °C

12: 72 percent / 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 36 h / 65 °C

13: 78 mol / Pd(dppf)Cl₂*CH₂Cl₂; K₂CO₃ / 1,2-dimethoxy-ethane / 12 h / Heating

14: 94 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2.33 h / 25 - 45 °C

15: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 2 h / 0 °C

16: 0.895 g / dimethylsulfoxide / 0.25 h / 25 °C

With 1H-imidazole; lithium hydroxide; potassium fluoride on basic alumina; lithium borohydride; thionyl chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; titanium tetrachloride; sodium cyanoborohydride; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; ytterbium(III) triflate; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile; 2: Fridel-Crafts reaction / 13: Suzuki coupling;
DOI:10.1021/ja040093a

Reference yield:

: 570377-04-7
2-benzyloxycarbonylamino-3-[3-(7-bromo-2-oxo-2,3-dihydro-1H-indol-3-yl)-4-hydroxy-phenyl]-propionic acid methyl ester

: 570377-00-3
4-(3-{1'-benzyl-3'-formyl-3-[2-(methoxyimino-methyl)-oxazol-5-yl]-1-methoxymethyl-2',3'-dihydro-1H,1'H-[4,7']biindolyl-3'-yl}-4-benzyloxy-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 97 percent / LiBH₄ / tetrahydrofuran / 2 h / 25 °C

2: 98 percent / p-TsOH / acetone / 2 h / 25 °C

3: Et₃N / CH₂Cl₂ / 2 h / 0 °C

4: 7.38 g / aq. Yb(OTf)3 / tetrahydrofuran / 24 h / 25 °C

5: 84 percent / imidazole / CH₂Cl₂ / 6 h / 25 °C

6: 80 percent / LiOH / dimethylformamide / 5 h / 25 °C

7: 85 percent / KF*alumina / 1,2-dimethoxy-ethane / 12 h / 25 °C

8: 72 percent / 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 36 h / 65 °C

9: 78 mol / Pd(dppf)Cl₂*CH₂Cl₂; K₂CO₃ / 1,2-dimethoxy-ethane / 12 h / Heating

10: 94 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2.33 h / 25 - 45 °C

11: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 2 h / 0 °C

12: 0.895 g / dimethylsulfoxide / 0.25 h / 25 °C

With 1H-imidazole; lithium hydroxide; potassium fluoride on basic alumina; lithium borohydride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; ytterbium(III) triflate; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 9: Suzuki coupling;
DOI:10.1021/ja040093a