(4S,5R)-4-[(R)-2-(Diethoxy-phosphoryl)-2,2-difluoro-1-hydroxy-ethyl]-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(4S,5R)-4-[(R)-2-(Diethoxy-phosphoryl)-2,2-difluoro-1-hydroxy-ethyl]-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:528523-50-4
Molecular Formula:C₂₂H₃₄F₂NO₇P
Molecular Weight:493.485
Hs Code.:

Synonyms:(4S,5R)-4-[(R)-2-(Diethoxy-phosphoryl)-2,2-difluoro-1-hydroxy-ethyl]-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Chemical Property of (4S,5R)-4-[(R)-2-(Diethoxy-phosphoryl)-2,2-difluoro-1-hydroxy-ethyl]-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of (4S,5R)-4-[(R)-2-(Diethoxy-phosphoryl)-2,2-difluoro-1-hydroxy-ethyl]-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 9 articles about (4S,5R)-4-[(R)-2-(Diethoxy-phosphoryl)-2,2-difluoro-1-hydroxy-ethyl]-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 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:

: 1478-53-1
Diethyl difluoromethylphosphonate

: 528523-49-1
(4R,5R)-4-Formyl-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 528523-50-4
(4S,5R)-4-[(R)-2-(Diethoxy-phosphoryl)-2,2-difluoro-1-hydroxy-ethyl]-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Diethyl difluoromethylphosphonate; With lithium diisopropyl amide; In tetrahydrofuran;

(4R,5R)-4-Formyl-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester; In tetrahydrofuran; at -78 - -70 ℃; for 4h;
DOI:10.1016/S0960-894X(02)00888-0

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 528523-50-4
(4S,5R)-4-[(R)-2-(Diethoxy-phosphoryl)-2,2-difluoro-1-hydroxy-ethyl]-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 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

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

Reference yield:

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

: 528523-50-4
(4S,5R)-4-[(R)-2-(Diethoxy-phosphoryl)-2,2-difluoro-1-hydroxy-ethyl]-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 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

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