[(1S)-1-{(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethylcarbamoyl}-2-(trityl-carbamoyl)-ethyl]-carbamic acid benzyl ester

Base Information

Chemical Name:[(1S)-1-{(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethylcarbamoyl}-2-(trityl-carbamoyl)-ethyl]-carbamic acid benzyl ester
CAS No.:333405-50-8
Molecular Formula:C₄₆H₄₆N₆O₆
Molecular Weight:778.908
Hs Code.:

Synonyms:[(1S)-1-{(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethylcarbamoyl}-2-(trityl-carbamoyl)-ethyl]-carbamic acid benzyl ester

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Chemical Property of [(1S)-1-{(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethylcarbamoyl}-2-(trityl-carbamoyl)-ethyl]-carbamic acid benzyl ester

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Technology Process of [(1S)-1-{(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethylcarbamoyl}-2-(trityl-carbamoyl)-ethyl]-carbamic acid benzyl ester

There total 6 articles about [(1S)-1-{(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethylcarbamoyl}-2-(trityl-carbamoyl)-ethyl]-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:

: (3R,5S)-5-((S)-1-Amino-2-phenyl-ethyl)-3-(3-azido-propyl)-dihydro-furan-2-one; hydrochloride

: 132388-57-9
N-benzyloxycarbonyl-N'-trityl-L-asparagine

: 333405-50-8
[(1S)-1-{(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethylcarbamoyl}-2-(trityl-carbamoyl)-ethyl]-carbamic acid benzyl ester

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1021/ol015612i

Reference yield:

: 133333-27-4
tert-butyl (1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate

: 333405-50-8
[(1S)-1-{(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethylcarbamoyl}-2-(trityl-carbamoyl)-ethyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

1.2: 62 percent / DMPU / tetrahydrofuran / 1.75 h / -78 - -50 °C

2.1: catecholborane; Rh(PPh₃)3Cl / tetrahydrofuran / 0.67 h / 20 °C

2.2: 70 percent / aq. H₂O₂; phosphate buffer / tetrahydrofuran; ethanol / 0 - 20 °C / pH 7.2

3.1: triethylamine / toluene / 0 - 20 °C

4.1: NaN₃; Bu₄NBr / H₂O; toluene / 3 h / Heating

5.1: aq. HCl / dioxane; tetrahydrofuran / 1 h / 20 °C

6.1: HOBT; EDCI; DIEA / dimethylformamide / 0 - 20 °C

With hydrogenchloride; Wilkinson's catalyst; sodium azide; tetrabutylammomium bromide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; benzo[1,3,2]dioxaborole; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol015612i

Reference yield:

: 137281-77-7
{(1S)-1-[(4R)-4-allyl-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

: 333405-50-8
[(1S)-1-{(1S)-1-[(4R)-4-(3-azido-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethylcarbamoyl}-2-(trityl-carbamoyl)-ethyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: catecholborane; Rh(PPh₃)3Cl / tetrahydrofuran / 0.67 h / 20 °C

1.2: 70 percent / aq. H₂O₂; phosphate buffer / tetrahydrofuran; ethanol / 0 - 20 °C / pH 7.2

2.1: triethylamine / toluene / 0 - 20 °C

3.1: NaN₃; Bu₄NBr / H₂O; toluene / 3 h / Heating

4.1: aq. HCl / dioxane; tetrahydrofuran / 1 h / 20 °C

5.1: HOBT; EDCI; DIEA / dimethylformamide / 0 - 20 °C

With hydrogenchloride; Wilkinson's catalyst; sodium azide; tetrabutylammomium bromide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; benzo[1,3,2]dioxaborole; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol015612i