(4S,5S)-4-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2(S)-(hydroxymethyl)-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)-(hydroxymethyl)-4-phenyl-4(E)-butenyl)-1,3-oxazolidine
CAS No.:161815-94-7
Molecular Formula:C₂₈H₃₇NO₄
Molecular Weight:451.606
Hs Code.:

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

There total 6 articles about (4S,5S)-4-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5-(2(S)-(hydroxymethyl)-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:

: 72155-45-4
Boc-L-phenylalaninal

: 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

Guidance literature:: Multi-step reaction with 5 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

With sodium hydroxide; dimethylsulfide borane complex; boron trifluoride diethyl etherate; dihydrogen peroxide; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; cyclohexene; In diethyl ether; 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

: 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

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 143006-56-8
(4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-5-(2-(chloromethyl)-3-propenyl)-2,2-dimethyl-1,3-oxazolidine

: 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

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / DMSO, NaHCO₃ / toluene / 20 h / 110 °C

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

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

With sodium hydroxide; dimethylsulfide borane complex; dihydrogen peroxide; sodium hydrogencarbonate; dimethyl sulfoxide; cyclohexene; In diethyl ether; toluene;
DOI:10.1021/jo00093a006