benzyl (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(diethylphosphonodifluoromethyl)butanoate

Base Information

Chemical Name:benzyl (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(diethylphosphonodifluoromethyl)butanoate
CAS No.:292601-95-7
Molecular Formula:C₂₁H₃₂F₂NO₇P
Molecular Weight:479.458
Hs Code.:

Synonyms:benzyl (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(diethylphosphonodifluoromethyl)butanoate

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Chemical Property of benzyl (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(diethylphosphonodifluoromethyl)butanoate

Chemical Property:

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Technology Process of benzyl (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(diethylphosphonodifluoromethyl)butanoate

There total 8 articles about benzyl (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(diethylphosphonodifluoromethyl)butanoate 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: 74.5%

: 717098-57-2
(2R,2'R,3'R)-N-[2'-(tert-butoxycarbonyl)amino-3'-(diethylphosphonodifluoromethyl)butanoyl]bornane-10,2-sultam

: 100-51-6,185532-71-2
benzyl alcohol

: 292601-95-7
benzyl (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(diethylphosphonodifluoromethyl)butanoate

Guidance literature:: With titanium(IV) isopropylate; In toluene; at 120 ℃; for 5h;
DOI:10.1021/jo000169v

Reference yield:

: 1026693-49-1
(Z)-4-(Diethoxy-phosphoryl)-4,4-difluoro-3-methyl-but-2-enoic acid

: 292601-95-7
benzyl (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(diethylphosphonodifluoromethyl)butanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: Et₃N / tetrahydrofuran / -78 - 4 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

2.2: 81.1 percent / tetrahydrofuran / 1 h / -78 °C

3.1: 88.8 percent / H₂ / Pd/C / ethyl acetate / 10 h / 20 °C

4.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

4.2: 1-chloro-1-nitrosocyclohexane / tetrahydrofuran / 0.5 h / -78 °C

5.1: AcOH; aq. HCl; Zn dust / tetrahydrofuran / 2 h / 20 °C

6.1: acetonitrile / 12 h / 20 °C

7.1: 74.5 percent / Ti(OiPr)4 / toluene / 5 h / 120 °C

With titanium(IV) isopropylate; hydrogenchloride; n-butyllithium; hydrogen; sodium hexamethyldisilazane; acetic acid; triethylamine; zinc; palladium on activated charcoal; In tetrahydrofuran; hexane; ethyl acetate; toluene; acetonitrile; 1.1: Substitution / 2.1: Metallation / 2.2: Acylation / 3.1: Catalytic hydrogenation / 4.1: Metallation / 4.2: Substitution / 5.1: Reduction / 6.1: Acylation / 7.1: Substitution;
DOI:10.1021/jo000169v

Reference yield:

: C₁₄H₂₃F₂O₆P

: 292601-95-7
benzyl (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(diethylphosphonodifluoromethyl)butanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: 81.1 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 88.8 percent / H₂ / Pd/C / ethyl acetate / 10 h / 20 °C

3.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

3.2: 1-chloro-1-nitrosocyclohexane / tetrahydrofuran / 0.5 h / -78 °C

4.1: AcOH; aq. HCl; Zn dust / tetrahydrofuran / 2 h / 20 °C

5.1: acetonitrile / 12 h / 20 °C

6.1: 74.5 percent / Ti(OiPr)4 / toluene / 5 h / 120 °C

With titanium(IV) isopropylate; hydrogenchloride; n-butyllithium; hydrogen; sodium hexamethyldisilazane; acetic acid; zinc; palladium on activated charcoal; In tetrahydrofuran; hexane; ethyl acetate; toluene; acetonitrile; 1.1: Metallation / 1.2: Acylation / 2.1: Catalytic hydrogenation / 3.1: Metallation / 3.2: Substitution / 4.1: Reduction / 5.1: Acylation / 6.1: Substitution;
DOI:10.1021/jo000169v