(3S)-1-benzyl-6-benzyloxy-4-bromo-3-(tert-butyldimethylsilanyloxymethyl)indoline

Base Information

Chemical Name:(3S)-1-benzyl-6-benzyloxy-4-bromo-3-(tert-butyldimethylsilanyloxymethyl)indoline
CAS No.:556038-47-2
Molecular Formula:C₂₉H₃₆BrNO₂Si
Molecular Weight:538.6
Hs Code.:

Synonyms:(3S)-1-benzyl-6-benzyloxy-4-bromo-3-(tert-butyldimethylsilanyloxymethyl)indoline

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S)-1-benzyl-6-benzyloxy-4-bromo-3-(tert-butyldimethylsilanyloxymethyl)indoline

Chemical Property:

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Technology Process of (3S)-1-benzyl-6-benzyloxy-4-bromo-3-(tert-butyldimethylsilanyloxymethyl)indoline

There total 14 articles about (3S)-1-benzyl-6-benzyloxy-4-bromo-3-(tert-butyldimethylsilanyloxymethyl)indoline 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:

: 20455-07-6
p-nitrophenyl methanesulfonate

: 556038-47-2
(3S)-1-benzyl-6-benzyloxy-4-bromo-3-(tert-butyldimethylsilanyloxymethyl)indoline

Guidance literature:: Multi-step reaction with 15 steps

1.1: 100 percent / H₂ / Ra-Ni / ethyl acetate; ethanol / 24 h / 23 °C / 72400.7 Torr

2.1: 94.5 g / Br₂ / methanol; CH₂Cl₂ / 0.5 h / 0 - 23 °C

3.1: aq. NaNO₂; H₂SO₄ / acetonitrile / 0 °C

3.2: 96 percent / aq. KI / acetonitrile / 0.75 h

4.1: 100 percent / KOH / CH₂Cl₂; methanol / 0.08 h / 23 °C

5.1: 88 percent / K₂CO₃ / dimethylformamide / 1 h / 23 °C

6.1: n-BuLi / toluene; hexane / -78 °C

6.2: 4.18 g / toluene

7.1: aq. acetic acid / 3 h / 100 °C

8.1: H₅IO₆ / tetrahydrofuran / 0.08 h / 0 °C

9.1: 2.76 percent / NaBH₄ / methanol / 0.08 h / -78 °C

10.1: aq. HCl; Fe; FeCl₂ / ethanol / 2 h / Heating

11.1: 3.42 percent / aq. NaHCO₃ / CH₂Cl₂ / 0.08 h / 23 °C

12.1: K₂CO₃ / dimethylformamide / 1 h / 23 °C

13.1: 1.91 g / PhSH / dimethylformamide / 1 h / 23 °C

14.1: 67 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C

15.1: 100 percent / imidazole / dimethylformamide / 0.17 h / 23 °C

With 1H-imidazole; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; sulfuric acid; hydrogen; bromine; cesium acetate; iron; sodium hydrogencarbonate; potassium carbonate; acetic acid; thiophenol; periodic acid; iron(II) chloride; sodium nitrite; Ra-Ni; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/ja035303i

Reference yield:

: 24690-19-5
methanesulfonic acid 4-aminophenyl ester

: 556038-47-2
(3S)-1-benzyl-6-benzyloxy-4-bromo-3-(tert-butyldimethylsilanyloxymethyl)indoline

Guidance literature:: Multi-step reaction with 14 steps

1.1: 94.5 g / Br₂ / methanol; CH₂Cl₂ / 0.5 h / 0 - 23 °C

2.1: aq. NaNO₂; H₂SO₄ / acetonitrile / 0 °C

2.2: 96 percent / aq. KI / acetonitrile / 0.75 h

3.1: 100 percent / KOH / CH₂Cl₂; methanol / 0.08 h / 23 °C

4.1: 88 percent / K₂CO₃ / dimethylformamide / 1 h / 23 °C

5.1: n-BuLi / toluene; hexane / -78 °C

5.2: 4.18 g / toluene

6.1: aq. acetic acid / 3 h / 100 °C

7.1: H₅IO₆ / tetrahydrofuran / 0.08 h / 0 °C

8.1: 2.76 percent / NaBH₄ / methanol / 0.08 h / -78 °C

9.1: aq. HCl; Fe; FeCl₂ / ethanol / 2 h / Heating

10.1: 3.42 percent / aq. NaHCO₃ / CH₂Cl₂ / 0.08 h / 23 °C

11.1: K₂CO₃ / dimethylformamide / 1 h / 23 °C

12.1: 1.91 g / PhSH / dimethylformamide / 1 h / 23 °C

13.1: 67 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C

14.1: 100 percent / imidazole / dimethylformamide / 0.17 h / 23 °C

With 1H-imidazole; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; sulfuric acid; bromine; cesium acetate; iron; sodium hydrogencarbonate; potassium carbonate; acetic acid; thiophenol; periodic acid; iron(II) chloride; sodium nitrite; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/ja035303i

Reference yield:

: 556038-75-6
3,5-dibromo-4-iodophenyjl

: 556038-47-2
(3S)-1-benzyl-6-benzyloxy-4-bromo-3-(tert-butyldimethylsilanyloxymethyl)indoline

Guidance literature:: Multi-step reaction with 11 steps

1.1: 88 percent / K₂CO₃ / dimethylformamide / 1 h / 23 °C

2.1: n-BuLi / toluene; hexane / -78 °C

2.2: 4.18 g / toluene

3.1: aq. acetic acid / 3 h / 100 °C

4.1: H₅IO₆ / tetrahydrofuran / 0.08 h / 0 °C

5.1: 2.76 percent / NaBH₄ / methanol / 0.08 h / -78 °C

6.1: aq. HCl; Fe; FeCl₂ / ethanol / 2 h / Heating

7.1: 3.42 percent / aq. NaHCO₃ / CH₂Cl₂ / 0.08 h / 23 °C

8.1: K₂CO₃ / dimethylformamide / 1 h / 23 °C

9.1: 1.91 g / PhSH / dimethylformamide / 1 h / 23 °C

10.1: 67 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C

11.1: 100 percent / imidazole / dimethylformamide / 0.17 h / 23 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; cesium acetate; iron; sodium hydrogencarbonate; potassium carbonate; acetic acid; thiophenol; periodic acid; iron(II) chloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja035303i