(S)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-4,4-difluorohexanoic acid

Base Information

Chemical Name:(S)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-4,4-difluorohexanoic acid
CAS No.:650604-90-3
Molecular Formula:C₁₉H₂₆F₂N₂O₆
Molecular Weight:416.422
Hs Code.:

Synonyms:(S)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-4,4-difluorohexanoic acid

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Chemical Property of (S)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-4,4-difluorohexanoic acid

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Technology Process of (S)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-4,4-difluorohexanoic acid

There total 10 articles about (S)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-4,4-difluorohexanoic 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: 75.0%

: 650604-89-0
N-6-[(benzyloxy)carbonyl]-N-2-(tert-butoxycarbonyl)-4,4-difluoro-L-lysinol

: 650604-90-3
(S)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-4,4-difluorohexanoic acid

Guidance literature:: With ruthenium trichloride; sodium periodate; In acetonitrile; at 20 ℃; for 2.5h;
DOI:10.1039/b307563j

Reference yield:

: 153334-98-6
tert-butyl (4S)-4-(3-ethoxy-2,2-difluoro-3-oxopropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

: 650604-90-3
(S)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-4,4-difluorohexanoic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / DIBAL-H / toluene / 0.5 h / -65 °C

2: 80 percent / K₂CO₃ / tetrahydrofuran / 20 h / 20 °C

3: 91 percent / H₂ / Pd(OH)2/C / ethanol; acetic acid / 3 h / 20 °C / 3102.97 Torr

4: 78 percent / aq. NaHCO₃ / acetone / 18 h / 0 - 20 °C

5: 81 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

6: 71 percent / benzoyl peroxide; Et₃SiH / toluene / 3 h / Heating

7: aq. AcOH / 20 °C

8: 75 percent / RuCl₃*H₂O; NaIO₄ / acetonitrile / 2.5 h / 20 °C

With triethylsilane; dmap; ruthenium trichloride; sodium periodate; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; dibenzoyl peroxide; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; acetic acid; acetone; toluene; acetonitrile; 2: Henry reaction / 6: Barton reaction;
DOI:10.1039/b307563j

Reference yield:

: 650604-86-7
tert-butyl (4S)-4-(2,2-difluoro-3-hydroxy-4-nitrobutyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

: 650604-90-3
(S)-6-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)-4,4-difluorohexanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / H₂ / Pd(OH)2/C / ethanol; acetic acid / 3 h / 20 °C / 3102.97 Torr

2: 78 percent / aq. NaHCO₃ / acetone / 18 h / 0 - 20 °C

3: 81 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

4: 71 percent / benzoyl peroxide; Et₃SiH / toluene / 3 h / Heating

5: aq. AcOH / 20 °C

6: 75 percent / RuCl₃*H₂O; NaIO₄ / acetonitrile / 2.5 h / 20 °C

With triethylsilane; dmap; ruthenium trichloride; sodium periodate; hydrogen; sodium hydrogencarbonate; acetic acid; dibenzoyl peroxide; palladium dihydroxide; In ethanol; dichloromethane; acetic acid; acetone; toluene; acetonitrile; 4: Barton reaction;
DOI:10.1039/b307563j