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

Base Information

Chemical Name:(4S,5S)-4-Benzyl-5-((E)-(S)-2-formyl-4-phenyl-but-3-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:161758-51-6
Molecular Formula:C₂₈H₃₅NO₄
Molecular Weight:449.59
Hs Code.:

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

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Chemical Property of (4S,5S)-4-Benzyl-5-((E)-(S)-2-formyl-4-phenyl-but-3-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of (4S,5S)-4-Benzyl-5-((E)-(S)-2-formyl-4-phenyl-but-3-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 7 articles about (4S,5S)-4-Benzyl-5-((E)-(S)-2-formyl-4-phenyl-but-3-enyl)-2,2-dimethyl-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:

: 161815-94-7
(4S,5S)-4-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2(S)-(hydroxymethyl)-4-phenyl-4(E)-butenyl)-1,3-oxazolidine

: 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

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 ℃; for 0.333333h;
DOI:10.1021/jo00093a006

Reference yield:

: 72155-45-4
Boc-L-phenylalaninal

: 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

Guidance literature:: Multi-step reaction with 6 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

With sodium hydroxide; 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;
DOI:10.1021/jo00093a006

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 5 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

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