(4S,5S)-4-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2(S)-carboxy-4-phenyl-4(E)-butenyl)-1,3-oxazolidine

Base Information

Chemical Name:(4S,5S)-4-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2(S)-carboxy-4-phenyl-4(E)-butenyl)-1,3-oxazolidine
CAS No.:161758-52-7
Molecular Formula:C₂₈H₃₅NO₅
Molecular Weight:465.59
Hs Code.:

Synonyms:(4S,5S)-4-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2(S)-carboxy-4-phenyl-4(E)-butenyl)-1,3-oxazolidine

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Chemical Property of (4S,5S)-4-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2(S)-carboxy-4-phenyl-4(E)-butenyl)-1,3-oxazolidine

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Technology Process of (4S,5S)-4-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2(S)-carboxy-4-phenyl-4(E)-butenyl)-1,3-oxazolidine

There total 8 articles about (4S,5S)-4-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2(S)-carboxy-4-phenyl-4(E)-butenyl)-1,3-oxazolidine 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:

: 161758-51-6
(4S,5S)-4-Benzyl-5-((E)-(S)-2-formyl-4-phenyl-but-3-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 161758-52-7
(4S,5S)-4-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2(S)-carboxy-4-phenyl-4(E)-butenyl)-1,3-oxazolidine

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; In tert-butyl alcohol; at 40 ℃; for 4h; Yield given;
DOI:10.1021/jo00093a006

Reference yield:

: 72155-45-4
Boc-L-phenylalaninal

: 161758-52-7
(4S,5S)-4-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2(S)-carboxy-4-phenyl-4(E)-butenyl)-1,3-oxazolidine

Guidance literature:: Multi-step reaction with 7 steps

1: 72 percent / BF₃*Et₂O / CHCl₃ / 5 h / -60 °C

2: 84 percent / p-TsOH / 46 h / Ambient temperature

3: 82 percent / DMSO, NaHCO₃ / toluene / 20 h / 110 °C

4: 73 percent / NaOH / diethyl ether / 1.) reflux, 20 min, 2.) room temp., 2 h

5: 1.) BH₃*(CH₃)2S, cyclohexene, 2.) 3 M NaOH , 30percent H₂O₂ / 1.) THF, 3 h; room temp., overnight, 2.) EtOH, room temp., 4 h

6: oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.33 h / -60 °C

7: aq. NaClO₂, aq. NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s) / 4 h / 40 °C

With sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; dimethylsulfide borane complex; boron trifluoride diethyl etherate; dihydrogen peroxide; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; cyclohexene; In diethyl ether; dichloromethane; chloroform; toluene; tert-butyl alcohol;
DOI:10.1021/jo00093a006

Reference yield:

: 143006-54-6
(4S,5S)-5-((tert-butoxycarbonyl)amino)-2-(chloromethyl)-6-phenyl-1-hexen-4-ol

: 161758-52-7
(4S,5S)-4-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2(S)-carboxy-4-phenyl-4(E)-butenyl)-1,3-oxazolidine

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / p-TsOH / 46 h / Ambient temperature

2: 82 percent / DMSO, NaHCO₃ / toluene / 20 h / 110 °C

3: 73 percent / NaOH / diethyl ether / 1.) reflux, 20 min, 2.) room temp., 2 h

4: 1.) BH₃*(CH₃)2S, cyclohexene, 2.) 3 M NaOH , 30percent H₂O₂ / 1.) THF, 3 h; room temp., overnight, 2.) EtOH, room temp., 4 h

5: oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.33 h / -60 °C

6: aq. NaClO₂, aq. NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s) / 4 h / 40 °C

With sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; cyclohexene; In diethyl ether; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1021/jo00093a006