(4S,5S)-4-benzyl-5-[(2S)-2-benzyl-3-hydroxypropyl]-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine

Base Information

Chemical Name:(4S,5S)-4-benzyl-5-[(2S)-2-benzyl-3-hydroxypropyl]-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine
CAS No.:143006-65-9
Molecular Formula:C₂₇H₃₇NO₄
Molecular Weight:439.595
Hs Code.:

Synonyms:(4S,5S)-4-benzyl-5-[(2S)-2-benzyl-3-hydroxypropyl]-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine

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Chemical Property of (4S,5S)-4-benzyl-5-[(2S)-2-benzyl-3-hydroxypropyl]-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine

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Technology Process of (4S,5S)-4-benzyl-5-[(2S)-2-benzyl-3-hydroxypropyl]-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine

There total 5 articles about (4S,5S)-4-benzyl-5-[(2S)-2-benzyl-3-hydroxypropyl]-3-(tert-butoxycarbonyl)-2,2-dimethyl-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: 55.0%

: 143006-60-4
(4S,5S)-4-benzyl-5-(2-benzyl-3-propenyl)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine

: 143006-63-7
(4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-5-((2R)-3-hydroxy-2-benzylpropyl)-2,2-dimethyl-1,3-oxazolidine

: 143006-65-9
(4S,5S)-4-benzyl-5-[(2S)-2-benzyl-3-hydroxypropyl]-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine

Guidance literature:: (4S,5S)-4-benzyl-5-(2-benzyl-3-propenyl)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine; With dimethylsulfide borane complex; In tetrahydrofuran; at 0 ℃; for 24h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; ethanol; at 20 ℃; for 10h;
DOI:10.1055/s-2003-37649

Reference yield:

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

: 143006-65-9
(4S,5S)-4-benzyl-5-[(2S)-2-benzyl-3-hydroxypropyl]-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine

Guidance literature:: Multi-step reaction with 4 steps

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

2: NaI / acetone / 12 h

3: 1) CuCN / 1) THF, cyclohexane, a) 30 min, -23 deg C, b) 30 min, 0 deg C, 2) THF, rt, 1 h

4: 1) BH₃*THF, 2) 30percent H₂O₂, 3 M NaOH / 1) THF, 3 h, 0 deg C, 2) EtOH, rt, 4 h

With sodium hydroxide; borane-THF; dihydrogen peroxide; toluene-4-sulfonic acid; sodium iodide; In acetone;
DOI:10.1021/jo00045a045

Reference yield:

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

: 143006-65-9
(4S,5S)-4-benzyl-5-[(2S)-2-benzyl-3-hydroxypropyl]-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine

Guidance literature:: Multi-step reaction with 3 steps

1: NaI / acetone / 12 h

2: 1) CuCN / 1) THF, cyclohexane, a) 30 min, -23 deg C, b) 30 min, 0 deg C, 2) THF, rt, 1 h

3: 1) BH₃*THF, 2) 30percent H₂O₂, 3 M NaOH / 1) THF, 3 h, 0 deg C, 2) EtOH, rt, 4 h

With sodium hydroxide; borane-THF; dihydrogen peroxide; sodium iodide; In acetone;
DOI:10.1021/jo00045a045