(2R)-2-(3-azido-propyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-(4S)-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid

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Chemical Name:(2R)-2-(3-azido-propyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-(4S)-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid
CAS No.:333405-56-4
Molecular Formula:C₅₂H₆₂N₆O₇Si
Molecular Weight:911.186
Hs Code.:

(2R)-2-(3-azido-propyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-(4S)-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid

Synonyms:(2R)-2-(3-azido-propyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-(4S)-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid

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Chemical Property of (2R)-2-(3-azido-propyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-(4S)-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid

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Technology Process of (2R)-2-(3-azido-propyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-(4S)-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid

There total 8 articles about (2R)-2-(3-azido-propyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-(4S)-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic 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:

: 18162-48-6
tert-butyldimethylsilyl chloride

: (2R,4S,5S)-2-(3-Azido-propyl)-5-[(S)-2-benzyloxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-4-hydroxy-6-phenyl-hexanoic acid

: 333405-56-4
(2R)-2-(3-azido-propyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-(4S)-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 44h;
DOI:10.1021/ol015612i

Reference yield:

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

: 333405-56-4
(2R)-2-(3-azido-propyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-(4S)-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid

Guidance literature:: Multi-step reaction with 3 steps

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

2: aq. LiOH / dioxane / 20 °C

3: 0.093 g / imidazole / dimethylformamide / 44 h / 20 °C

With 1H-imidazole; lithium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; N,N-dimethyl-formamide;
DOI:10.1021/ol015612i

Reference yield:

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

: 333405-56-4
(2R)-2-(3-azido-propyl)-(5S)-5-[(2S)-2-benzyloxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-(4S)-4-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-hexanoic acid

Guidance literature:: Multi-step reaction with 8 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

7.1: aq. LiOH / dioxane / 20 °C

8.1: 0.093 g / imidazole / dimethylformamide / 44 h / 20 °C

With 1H-imidazole; hydrogenchloride; lithium hydroxide; 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