tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-isopropyl-6-phenylhex-3-enoate

Base Information

Chemical Name:tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-isopropyl-6-phenylhex-3-enoate
CAS No.:461696-69-5
Molecular Formula:C₂₄H₃₇NO₄
Molecular Weight:403.562
Hs Code.:

Synonyms:tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-isopropyl-6-phenylhex-3-enoate

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Chemical Property of tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-isopropyl-6-phenylhex-3-enoate

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Technology Process of tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-isopropyl-6-phenylhex-3-enoate

There total 2 articles about tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-isopropyl-6-phenylhex-3-enoate 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: 84.0%

: 1068-55-9
isopropylmagnesium chloride

: 388077-08-5
tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-methylsulfonyloxy-6-phenylhex-2-enoate

: 461696-69-5
tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-isopropyl-6-phenylhex-3-enoate

Guidance literature:: isopropylmagnesium chloride; In tetrahydrofuran; at 0 ℃; for 0.25h;

With boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃; for 0.0833333h;

tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-methylsulfonyloxy-6-phenylhex-2-enoate; In tetrahydrofuran; at -78 ℃; for 0.5h; Further stages.;
DOI:10.1021/jo025923m

Reference yield:

: 461696-68-4
tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhex-2-enoate

: 461696-69-5
tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-isopropyl-6-phenylhex-3-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 90 percent / pyridine / CHCl₃ / 1 h / 0 °C

2.1: CuCN / tetrahydrofuran / 0.25 h / 0 °C

2.2: BF₃*Et₂O / tetrahydrofuran / 0.08 h / -78 °C

2.3: 84 percent / tetrahydrofuran / 0.5 h / -78 °C

With pyridine; In tetrahydrofuran; chloroform;
DOI:10.1021/jo025923m

Reference yield:

: 461696-69-5
tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-isopropyl-6-phenylhex-3-enoate

: [(E)-(3S,9S,12R,15R)-15-Benzyl-9-(3-guanidino-propyl)-12-isopropyl-2,5,8,11-tetraoxo-1,4,7,10-tetraaza-cyclopentadec-13-en-3-yl]-acetic acid; compound with trifluoro-acetic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 20 °C

2: 379 mg / triethylamine / CHCl₃; dimethylformamide; H₂O / 3 h / 20 °C

3: 527 mg / 1-hydroxybenzotriazole monohydrate; N,N'-dicyclohexylcarbodiimide; (i-Pr)2NEt / dimethylformamide / 0 °C

4: 99 percent / LiOH / H₂O; methanol / 3 h / 20 °C

5: trifluoroacetic acid / methoxybenzene / 2 h / 20 °C

6: 466 mg / Et₃N / dimethylformamide / 20 °C

7: N,N'-dicyclohexylcarbodiimide / ethyl acetate / 3 h / 20 °C

8: HCl / dioxane / 0.5 h / 20 °C

9: 145 mg / N-methylmorpholine / dimethylformamide / 3 h / -20 °C / pH 8

10: 79 percent / TMSBr; thianisole; m-cresol / 1,2-ethanedithiol / 3 h / 0 °C

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; trimethylsilyl bromide; methyl-phenyl-thioether; 3-methyl-phenol; 1-hydroxybenzotriazol-hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; ethane-1,2-dithiol; In 1,4-dioxane; methanol; chloroform; water; ethyl acetate; methoxybenzene; N,N-dimethyl-formamide;
DOI:10.1021/jo025923m