diethyl (2R,3S,4R)-1,1-difluoro-2,4-dihydroxy-3-(palmitoylamino)-4-phenylbutylphosphonate

Base Information

Chemical Name:diethyl (2R,3S,4R)-1,1-difluoro-2,4-dihydroxy-3-(palmitoylamino)-4-phenylbutylphosphonate
CAS No.:528523-54-8
Molecular Formula:C₃₀H₅₂F₂NO₆P
Molecular Weight:591.717
Hs Code.:

Synonyms:diethyl (2R,3S,4R)-1,1-difluoro-2,4-dihydroxy-3-(palmitoylamino)-4-phenylbutylphosphonate

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Chemical Property of diethyl (2R,3S,4R)-1,1-difluoro-2,4-dihydroxy-3-(palmitoylamino)-4-phenylbutylphosphonate

Chemical Property:

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Technology Process of diethyl (2R,3S,4R)-1,1-difluoro-2,4-dihydroxy-3-(palmitoylamino)-4-phenylbutylphosphonate

There total 10 articles about diethyl (2R,3S,4R)-1,1-difluoro-2,4-dihydroxy-3-(palmitoylamino)-4-phenylbutylphosphonate 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:

: ((2R,3R,4R)-3-Amino-1,1-difluoro-2,4-dihydroxy-4-phenyl-butyl)-phosphonic acid diethyl ester

: 112-67-4
n-hexadecanoyl chloride

: 528523-54-8
diethyl (2R,3S,4R)-1,1-difluoro-2,4-dihydroxy-3-(palmitoylamino)-4-phenylbutylphosphonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/S0960-894X(02)00888-0

Reference yield:

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 528523-54-8
diethyl (2R,3S,4R)-1,1-difluoro-2,4-dihydroxy-3-(palmitoylamino)-4-phenylbutylphosphonate

Guidance literature:: Multi-step reaction with 10 steps

1.1: methanol / 0.5 h

2.1: imidazole / dimethylformamide / 13.5 h / 20 - 60 °C

3.1: 40.6 g / triphenyl phosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 12 h / 20 °C

4.1: 77 percent / DIBAL-H / CH₂Cl₂ / 1.5 h / -20 °C

5.1: p-TsOH / benzene / 0.5 h / Heating

6.1: tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 60 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

8.1: LDA / tetrahydrofuran

8.2: tetrahydrofuran / 4 h / -78 - -70 °C

9.1: 3 M aq. HCl / ethyl acetate / 1 h / 20 °C

10.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene; 3.1: Mitsunobu inversion;
DOI:10.1016/S0960-894X(02)00888-0

Reference yield:

: 167082-56-6
tert-butyl [(1S,2S)-1,3-dihydroxy-1-phenylpropan-2-yl]carbamate

: 528523-54-8
diethyl (2R,3S,4R)-1,1-difluoro-2,4-dihydroxy-3-(palmitoylamino)-4-phenylbutylphosphonate

Guidance literature:: Multi-step reaction with 9 steps

1.1: imidazole / dimethylformamide / 13.5 h / 20 - 60 °C

2.1: 40.6 g / triphenyl phosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 12 h / 20 °C

3.1: 77 percent / DIBAL-H / CH₂Cl₂ / 1.5 h / -20 °C

4.1: p-TsOH / benzene / 0.5 h / Heating

5.1: tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 60 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

7.1: LDA / tetrahydrofuran

7.2: tetrahydrofuran / 4 h / -78 - -70 °C

8.1: 3 M aq. HCl / ethyl acetate / 1 h / 20 °C

9.1: Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene; 2.1: Mitsunobu inversion;
DOI:10.1016/S0960-894X(02)00888-0