(S)-1-((S)-2-{(S)-2-[(3S,4R)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexanoyloxy]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(S)-1-((S)-2-{(S)-2-[(3S,4R)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexanoyloxy]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester
CAS No.:876954-01-7
Molecular Formula:C₄₁H₆₉N₃O₉Si
Molecular Weight:776.099
Hs Code.:

(S)-1-((S)-2-{(S)-2-[(3S,4R)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexanoyloxy]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester

Synonyms:(S)-1-((S)-2-{(S)-2-[(3S,4R)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexanoyloxy]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester

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Chemical Property of (S)-1-((S)-2-{(S)-2-[(3S,4R)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexanoyloxy]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester

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Technology Process of (S)-1-((S)-2-{(S)-2-[(3S,4R)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexanoyloxy]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester

There total 11 articles about (S)-1-((S)-2-{(S)-2-[(3S,4R)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexanoyloxy]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic 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: 59.0%

: 766513-79-5
(3S,4R)-4-(tert-butoxycarbonylamino)-5-methyl-3-(tert-butyldimethylsilanyloxy)hexanoic acid

: 387823-12-3
N-(N-(α-hydroxyisovaleryl)leucyl)proline benzyl ester

: 876954-01-7
(S)-1-((S)-2-{(S)-2-[(3S,4R)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexanoyloxy]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at -5 ℃; for 7h;
DOI:10.1021/ol0530023

Reference yield:

: 17407-55-5
(S)-2-Hydroxy-3-methylbutanoic acid

: 876954-01-7
(S)-1-((S)-2-{(S)-2-[(3S,4R)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexanoyloxy]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 84 percent / N-methylmorpholine; N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 14 h / 20 °C

2: 59 percent / 4-(dimethylamino)pyridine; N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 7 h / -5 °C

With 4-methyl-morpholine; dmap; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1021/jo070412r

Reference yield:

: 22838-58-0
Boc-D-Val-OH

: 876954-01-7
(S)-1-((S)-2-{(S)-2-[(3S,4R)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hexanoyloxy]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / pyridine / 1 h / 20 °C

2: 61 percent / lithium diisopropylamide / tetrahydrofuran / 0.75 h / -78 °C

3: 92 percent / potassium borohydride / methanol / 0.83 h / -78 - 0 °C

4: 98 percent / imidazole / dimethylformamide / 18.5 h / 0 - 20 °C

5: 70 percent / NaOH / methanol; tetrahydrofuran; diethyl ether / 0 - 20 °C

6: 59 percent / 4-(dimethylamino)pyridine; N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 7 h / -5 °C

With pyridine; 1H-imidazole; dmap; sodium hydroxide; potassium borohydride; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo070412r