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

Base Information

• Chemical Name: [(1S)-1-{(4R)-4-[3-(tert-butyldimethylsilanyloxy)propyl]-5-oxo-tetrahydrofuran-(2R)-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid tert-butyl ester
• CAS No.: 817208-67-6
• Molecular Formula: C₄₁H₅₆N₂O₆Si
• Molecular Weight: 700.991
• Mol file: 817208-67-6.mol

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

Chemical Property of [(1S)-1-{(4R)-4-[3-(tert-butyldimethylsilanyloxy)propyl]-5-oxo-tetrahydrofuran-(2R)-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S)-1-{(4R)-4-[3-(tert-butyldimethylsilanyloxy)propyl]-5-oxo-tetrahydrofuran-(2R)-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid tert-butyl ester

There total 1 articles about [(1S)-1-{(4R)-4-[3-(tert-butyldimethylsilanyloxy)propyl]-5-oxo-tetrahydrofuran-(2R)-2-yl}-3-(tritylcarbamoyl)propyl]carbamic 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: 62.0%

[1-{4-[3-(tert-butyldimethylsilanyloxy)propyl]-5-oxo-2,5-dihydrofuran-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid tert-butyl ester → [(1S)-1-{(4R)-4-[3-(tert-butyldimethylsilanyloxy)propyl]-5-oxo-tetrahydrofuran-(2R)-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid tert-butyl ester (817208-67-6) + [(1S)-1-{(4S)-4-[3-(tert-butyldimethylsilanyloxy)propyl]-5-oxo-tetrahydrofuran-(2S)-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid tert-butyl ester

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol; for 3h;

DOI:10.1021/ol047880x

Reference yield:

[(1S)-1-{(4R)-4-[3-(tert-butyldimethylsilanyloxy)propyl]-5-oxo-tetrahydrofuran-(2R)-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid tert-butyl ester (817208-67-6) → [(S)-1-[(2R,4R)-4-(3-Hydroxy-propyl)-5-oxo-tetrahydro-furan-2-yl]-3-(trityl-carbamoyl)-propyl]-carbamic acid tert-butyl ester (817208-68-7)

Guidance literature:

With trifluoroacetic acid; In methanol; acetonitrile; at 20 ℃; for 1h;

DOI:10.1021/ol047880x

Reference yield:

[(1S)-1-{(4R)-4-[3-(tert-butyldimethylsilanyloxy)propyl]-5-oxo-tetrahydrofuran-(2R)-2-yl}-3-(tritylcarbamoyl)propyl]carbamic acid tert-butyl ester (817208-67-6) → (2R)-2-(3-azidopropyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(tritylcarbamoyl)propionylamino]-(4R)-4-(tert-butyldimethylsilanyloxy)-7-(tritylcarbamoyl)heptanoic acid (817208-73-4)

Guidance literature:

Multi-step reaction with 7 steps

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

2.1: diisopropylethylamine / toluene / 0 - 20 °C

3.1: 2.61 g / aq. NaN₃; Bu₄NBr / toluene / 3 h / Heating

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

4.2: TBAF / tetrahydrofuran; CH₂Cl₂ / 0 - 20 °C

5.1: 2.11 g / HOBt; EDCI / dimethylformamide / 14 h / 0 - 20 °C

6.1: aq. LiOH / dioxane / 0.33 h

7.1: 1.85 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; lithium hydroxide; sodium azide; t-butyldimethylsiyl triflate; tetrabutylammomium bromide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ol047880x

Downstream raw materials:

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

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

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

[1-[1-[4-(3-azidopropyl)-5-oxo-tetrahydrofuran-2-yl]-3-(tritylcarbamoyl)propylcarbamoyl]-2-(tritylcarbamoyl)ethyl]carbamic acid benzyl ester