(2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-6-phenylhexanoic acid

Base Information

Chemical Name:(2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-6-phenylhexanoic acid
CAS No.:98818-49-6
Molecular Formula:C₃₀H₄₅NO₅Si
Molecular Weight:527.777
Hs Code.:

Synonyms:(2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-6-phenylhexanoic acid

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Chemical Property of (2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-6-phenylhexanoic acid

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Technology Process of (2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-6-phenylhexanoic acid

There total 14 articles about (2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-6-phenylhexanoic 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: 92.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 98818-43-0
(2R,4R,5S)-2-Benzyl-5-(tert-butoxycarbonyl)amino-4-hydroxy-6-phenylhexanoic acid

: 98818-49-6
(2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-6-phenylhexanoic acid

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 96h; Ambient temperature;
DOI:10.1135/cccc19980541

Reference yield:

: 98737-42-9
(4R,5R)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one

: 98818-49-6
(2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-6-phenylhexanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: aq. LiOH / 1,2-dimethoxy-ethane / 6 h / 20 °C

2.1: imidazole / dimethylformamide / 15 h

2.2: 204 mg / dimethylformamide; methanol / 3 h

With 1H-imidazole; lithium hydroxide; In 1,2-dimethoxyethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2003-37649

Reference yield:

: 135130-98-2
(4R)-4-{1-[(S)-(tert-butoxycarbonyl)amino]-2-phenylethyl}-γ-butyrolactone

: 98818-49-6
(2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-6-phenylhexanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium diisopropylamide / hexane; tetrahydrofuran / 0.67 h / -78 °C

1.2: tetrahydrofuran; hexane / -78 °C

1.3: Ac₂O; Et₃N / 1 h / 120 °C

2.1: H₂ / Pd/C / ethyl acetate; methanol / 2 h / 2585.74 Torr

3.1: 3.6 g / LiOH; water; DME / 5 h / 20 °C

4.1: 3.4 g / imidazole; DMF

With 1H-imidazole; lithium hydroxide; 1,2-dimethoxyethane; water; hydrogen; N,N-dimethyl-formamide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; ethyl acetate;
DOI:10.1016/S0040-4020(00)01167-4