(2R)-2-(3-azidopropyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(tritylcarbamoyl)propionylamino]-(4R)-4-(tert-butyldimethylsilanyloxy)-7-(tritylcarbamoyl)heptanoic acid

Base Information

Chemical Name:(2R)-2-(3-azidopropyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(tritylcarbamoyl)propionylamino]-(4R)-4-(tert-butyldimethylsilanyloxy)-7-(tritylcarbamoyl)heptanoic acid
CAS No.:817208-73-4
Molecular Formula:C₆₇H₇₅N₇O₈Si
Molecular Weight:1134.46
Hs Code.:

(2R)-2-(3-azidopropyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(tritylcarbamoyl)propionylamino]-(4R)-4-(tert-butyldimethylsilanyloxy)-7-(tritylcarbamoyl)heptanoic acid

Synonyms:(2R)-2-(3-azidopropyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(tritylcarbamoyl)propionylamino]-(4R)-4-(tert-butyldimethylsilanyloxy)-7-(tritylcarbamoyl)heptanoic acid

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Chemical Property of (2R)-2-(3-azidopropyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(tritylcarbamoyl)propionylamino]-(4R)-4-(tert-butyldimethylsilanyloxy)-7-(tritylcarbamoyl)heptanoic acid

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Technology Process of (2R)-2-(3-azidopropyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(tritylcarbamoyl)propionylamino]-(4R)-4-(tert-butyldimethylsilanyloxy)-7-(tritylcarbamoyl)heptanoic acid

There total 8 articles about (2R)-2-(3-azidopropyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(tritylcarbamoyl)propionylamino]-(4R)-4-(tert-butyldimethylsilanyloxy)-7-(tritylcarbamoyl)heptanoic acid 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:

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

: 817208-73-4
(2R)-2-(3-azidopropyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(tritylcarbamoyl)propionylamino]-(4R)-4-(tert-butyldimethylsilanyloxy)-7-(tritylcarbamoyl)heptanoic acid

Guidance literature:: Multi-step reaction with 8 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: TBAF / tetrahydrofuran; CH₂Cl₂ / 0 - 20 °C

6.1: 2.11 g / HOBt; EDCI / dimethylformamide / 14 h / 0 - 20 °C

7.1: aq. LiOH / dioxane / 0.33 h

8.1: 1.85 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; lithium hydroxide; sodium azide; t-butyldimethylsiyl triflate; tetrabutylammomium bromide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; platinum(IV) oxide; In 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/ol047880x

Reference yield:

: (2R,4R,5S)-2-(3-Azido-propyl)-5-[(S)-2-benzyloxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-4-hydroxy-7-(trityl-carbamoyl)-heptanoic acid

: 69739-34-0
t-butyldimethylsiyl triflate

: 817208-73-4
(2R)-2-(3-azidopropyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(tritylcarbamoyl)propionylamino]-(4R)-4-(tert-butyldimethylsilanyloxy)-7-(tritylcarbamoyl)heptanoic acid

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ol047880x

Reference yield:

: (S)-4-Amino-4-[(2R,4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-2-yl]-N-trityl-butyramide

: 817208-73-4
(2R)-2-(3-azidopropyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(tritylcarbamoyl)propionylamino]-(4R)-4-(tert-butyldimethylsilanyloxy)-7-(tritylcarbamoyl)heptanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 2.11 g / HOBt; EDCI / dimethylformamide / 14 h / 0 - 20 °C

2: aq. LiOH / dioxane / 0.33 h

3: 1.85 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; lithium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol047880x