tert-butyl (1S,2S,4R)-5-{[(1S)-2-(benzylamino)-1-methyl-2-oxoethyl]amino}-2-{[tert-butyl(dimethyl)silyl]oxy}-1-isobutyl-4-methyl-5-oxopentylcarbamate

Base Information

• Chemical Name: tert-butyl (1S,2S,4R)-5-{[(1S)-2-(benzylamino)-1-methyl-2-oxoethyl]amino}-2-{[tert-butyl(dimethyl)silyl]oxy}-1-isobutyl-4-methyl-5-oxopentylcarbamate
• CAS No.: 849409-80-9
• Molecular Formula: C₃₁H₅₅N₃O₅Si
• Molecular Weight: 577.88
• Mol file: 849409-80-9.mol

Synonyms:tert-butyl (1S,2S,4R)-5-{[(1S)-2-(benzylamino)-1-methyl-2-oxoethyl]amino}-2-{[tert-butyl(dimethyl)silyl]oxy}-1-isobutyl-4-methyl-5-oxopentylcarbamate

Chemical Property of tert-butyl (1S,2S,4R)-5-{[(1S)-2-(benzylamino)-1-methyl-2-oxoethyl]amino}-2-{[tert-butyl(dimethyl)silyl]oxy}-1-isobutyl-4-methyl-5-oxopentylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (1S,2S,4R)-5-{[(1S)-2-(benzylamino)-1-methyl-2-oxoethyl]amino}-2-{[tert-butyl(dimethyl)silyl]oxy}-1-isobutyl-4-methyl-5-oxopentylcarbamate

There total 5 articles about tert-butyl (1S,2S,4R)-5-{[(1S)-2-(benzylamino)-1-methyl-2-oxoethyl]amino}-2-{[tert-butyl(dimethyl)silyl]oxy}-1-isobutyl-4-methyl-5-oxopentylcarbamate 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: 89.0%

tert-butyl (S)-[1-(benzylamino)-1-oxopropan-2-yl]carbamate (51814-55-2,140866-04-2) + (2R,4S,5S)-5-[(tert-butyloxycarbonyl)amino]-4-[(tert-butyldimethylsilyl)oxy]-2,7-dimethyloctanoic acid (271601-65-1) → tert-butyl (1S,2S,4R)-5-{[(1S)-2-(benzylamino)-1-methyl-2-oxoethyl]amino}-2-{[tert-butyl(dimethyl)silyl]oxy}-1-isobutyl-4-methyl-5-oxopentylcarbamate (849409-80-9)

Guidance literature:

tert-butyl (S)-[1-(benzylamino)-1-oxopropan-2-yl]carbamate; With hydrogenchloride; water; In ethyl acetate; for 2h;

(2R,4S,5S)-5-[(tert-butyloxycarbonyl)amino]-4-[(tert-butyldimethylsilyl)oxy]-2,7-dimethyloctanoic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 0 - 20 ℃;

Reference yield:

(5S,1'S)-5-<1'--3'-methylbutyl>dihydrofuran-2(3H)-one (105018-81-3) → tert-butyl (1S,2S,4R)-5-{[(1S)-2-(benzylamino)-1-methyl-2-oxoethyl]amino}-2-{[tert-butyl(dimethyl)silyl]oxy}-1-isobutyl-4-methyl-5-oxopentylcarbamate (849409-80-9)

Guidance literature:

Multi-step reaction with 4 steps

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

1.2: tetrahydrofuran / 0.5 h / -78 °C

2.1: aq. LiOH / tetrahydrofuran / 8 h / 23 °C

3.1: imidazole / dimethylformamide / 24 h

4.1: EDC; HOBt; iPr₂NEt / dimethylformamide; CH₂Cl₂ / 0 - 23 °C

With 1H-imidazole; lithium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0101803

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyl (1S,2S,4R)-5-{[(1S)-2-(benzylamino)-1-methyl-2-oxoethyl]amino}-2-{[tert-butyl(dimethyl)silyl]oxy}-1-isobutyl-4-methyl-5-oxopentylcarbamate (849409-80-9)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 24 h

2: EDC; HOBt; iPr₂NEt / dimethylformamide; CH₂Cl₂ / 0 - 23 °C

With 1H-imidazole; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0101803

upstream raw materials:

(5S,1'S)-5-<1'--3'-methylbutyl>dihydrofuran-2(3H)-one

tert-butyldimethylsilyl chloride

(3R,5S,1'S)-5-[1'-[(tert-butyloxycarbonyl)amino]-3'-methylbutyl]-3-methyldihydrofuran-2(3H)-one

(2R,4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-2,7-dimethyl-octanoic acid

Downstream raw materials:

{(S)-1-[(1S,2S,4R)-4-((S)-1-Benzylcarbamoyl-ethylcarbamoyl)-2-hydroxy-1-isobutyl-pentylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid tert-butyl ester

tert-butyl (1S,2S,4R)-5-{[(1S)-2-(benzylamino)-1-methyl-2-oxoethyl]amino}-2-hydroxy-1-isobutyl-4-methyl-5-oxopentylcarbamate