[1-{4-(3-azidopropyl)-5-oxo-tetrahydrofuran-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid benzyl ester

Base Information

Chemical Name:[1-{4-(3-azidopropyl)-5-oxo-tetrahydrofuran-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid benzyl ester
CAS No.:817208-70-1
Molecular Formula:C₃₈H₃₉N₅O₅
Molecular Weight:645.758
Hs Code.:

Synonyms:[1-{4-(3-azidopropyl)-5-oxo-tetrahydrofuran-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid benzyl ester

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Chemical Property of [1-{4-(3-azidopropyl)-5-oxo-tetrahydrofuran-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid benzyl ester

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Technology Process of [1-{4-(3-azidopropyl)-5-oxo-tetrahydrofuran-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid benzyl ester

There total 5 articles about [1-{4-(3-azidopropyl)-5-oxo-tetrahydrofuran-2-yl}-3-(tritylcarbamoyl)propyl]carbamic 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: 72.0%

: 817208-69-8
[(1S)-1-{(4R)-4-(3-azidopropyl)-5-oxo-tetrahydrofuran-(2R)-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid tert-butyl ester

: 100-39-0
benzyl bromide

: 817208-70-1
[1-{4-(3-azidopropyl)-5-oxo-tetrahydrofuran-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid benzyl ester

Guidance literature:: [(1S)-1-{(4R)-4-(3-azidopropyl)-5-oxo-tetrahydrofuran-(2R)-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid tert-butyl ester; With 2,6-dimethylpyridine; t-butyldimethylsiyl triflate; In dichloromethane; at 20 ℃; for 1h;

benzyl bromide; With tetrabutyl ammonium fluoride; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1021/ol047880x

Reference yield:

: [1-{4-[3-(tert-butyldimethylsilanyloxy)propyl]-5-oxo-2,5-dihydrofuran-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid tert-butyl ester

: 817208-70-1
[1-{4-(3-azidopropyl)-5-oxo-tetrahydrofuran-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 62 percent / H₂ / PtO₂ / ethanol / 3 h

2.1: aq. TFA / methanol; acetonitrile / 1 h / 20 °C

3.1: diisopropylethylamine / toluene / 0 - 20 °C

4.1: 2.61 g / aq. NaN₃; Bu₄NBr / toluene / 3 h / Heating

5.1: TBSOTf; 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

5.2: 72 percent / TBAF / CH₂Cl₂ / 2 h / 0 °C

With 2,6-dimethylpyridine; sodium azide; t-butyldimethylsiyl triflate; tetrabutylammomium bromide; hydrogen; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; platinum(IV) oxide; In methanol; ethanol; dichloromethane; toluene; acetonitrile;
DOI:10.1021/ol047880x

Reference yield:

: 817208-68-7
[(S)-1-[(2R,4R)-4-(3-Hydroxy-propyl)-5-oxo-tetrahydro-furan-2-yl]-3-(trityl-carbamoyl)-propyl]-carbamic acid tert-butyl ester

: 817208-70-1
[1-{4-(3-azidopropyl)-5-oxo-tetrahydrofuran-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisopropylethylamine / toluene / 0 - 20 °C

2.1: 2.61 g / aq. NaN₃; Bu₄NBr / toluene / 3 h / Heating

3.1: TBSOTf; 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

3.2: 72 percent / TBAF / CH₂Cl₂ / 2 h / 0 °C

With 2,6-dimethylpyridine; sodium azide; t-butyldimethylsiyl triflate; tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene;
DOI:10.1021/ol047880x