(4S,5S)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-benzyl-5-(1-ethynyl)-1,3-oxazolidine

Base Information

Chemical Name:(4S,5S)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-benzyl-5-(1-ethynyl)-1,3-oxazolidine
CAS No.:174510-91-9
Molecular Formula:C₁₉H₂₇NO₃
Molecular Weight:317.428
Hs Code.:

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

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

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

There total 5 articles about (4S,5S)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-benzyl-5-(1-ethynyl)-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: 85.0%

: 99113-28-7
(3S,4S)-5-[(tert-butoxycarbonyl)amino]-3-hydroxy-5-phenyl-1-pentene

: 77-76-9
2,2-dimethoxy-propane

: 174510-91-9
(4S,5S)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-benzyl-5-(1-ethynyl)-1,3-oxazolidine

Guidance literature:: With pyridinium p-toluenesulfonate; In toluene; at 80 ℃; for 4h;
DOI:10.1021/jo001072b

Reference yield:

: 63-91-2,25191-15-5,658-69-5,67675-33-6
L-phenylalanine

: 174510-91-9
(4S,5S)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-benzyl-5-(1-ethynyl)-1,3-oxazolidine

Guidance literature:: Multi-step reaction with 5 steps

1: LiAlH₄ / tetrahydrofuran

2: CH₂Cl₂

3: (COCl)2; DMSO; iPr₂NEt / CH₂Cl₂ / -35 - 0 °C

4: 2.7 g / tetrahydrofuran / 2 h / 20 °C

5: 85 percent / PPTS / toluene / 4 h / 80 °C

With lithium aluminium tetrahydride; oxalyl dichloride; pyridinium p-toluenesulfonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene; 1: Reduction / 2: Acylation / 3: Oxidation / 4: Grignard reaction / 5: Cyclization;
DOI:10.1021/jo001072b

Reference yield:

: 3182-95-4
L-Phenylalaninol

: 174510-91-9
(4S,5S)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-benzyl-5-(1-ethynyl)-1,3-oxazolidine

Guidance literature:: Multi-step reaction with 4 steps

1: CH₂Cl₂

2: (COCl)2; DMSO; iPr₂NEt / CH₂Cl₂ / -35 - 0 °C

3: 2.7 g / tetrahydrofuran / 2 h / 20 °C

4: 85 percent / PPTS / toluene / 4 h / 80 °C

With oxalyl dichloride; pyridinium p-toluenesulfonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene; 1: Acylation / 2: Oxidation / 3: Grignard reaction / 4: Cyclization;
DOI:10.1021/jo001072b