tert-butyl (4S)-(4-{[(benzyloxy)carbonyl]amino}-2,2-difluoro-3-hydroxybutyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Base Information

Chemical Name:tert-butyl (4S)-(4-{[(benzyloxy)carbonyl]amino}-2,2-difluoro-3-hydroxybutyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
CAS No.:650604-87-8
Molecular Formula:C₂₂H₃₂F₂N₂O₆
Molecular Weight:458.503
Hs Code.:

Synonyms:tert-butyl (4S)-(4-{[(benzyloxy)carbonyl]amino}-2,2-difluoro-3-hydroxybutyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

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Chemical Property of tert-butyl (4S)-(4-{[(benzyloxy)carbonyl]amino}-2,2-difluoro-3-hydroxybutyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

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Technology Process of tert-butyl (4S)-(4-{[(benzyloxy)carbonyl]amino}-2,2-difluoro-3-hydroxybutyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

There total 7 articles about tert-butyl (4S)-(4-{[(benzyloxy)carbonyl]amino}-2,2-difluoro-3-hydroxybutyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 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: 78.0%

: 75315-63-8
N-(benzyloxycarbonyl)succinimide

: 650604-96-9
4-(4-amino-2,2-difluoro-3-hydroxy-butyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 650604-87-8
tert-butyl (4S)-(4-{[(benzyloxy)carbonyl]amino}-2,2-difluoro-3-hydroxybutyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Guidance literature:: With sodium hydrogencarbonate; In acetone; at 0 - 20 ℃; for 18h;
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

: 650604-87-8
tert-butyl (4S)-(4-{[(benzyloxy)carbonyl]amino}-2,2-difluoro-3-hydroxybutyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 4 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

With hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; palladium dihydroxide; In tetrahydrofuran; ethanol; acetic acid; acetone; toluene; 2: Henry 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

: 650604-87-8
tert-butyl (4S)-(4-{[(benzyloxy)carbonyl]amino}-2,2-difluoro-3-hydroxybutyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 2 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

With hydrogen; sodium hydrogencarbonate; palladium dihydroxide; In ethanol; acetic acid; acetone;
DOI:10.1039/b307563j