(S)-4-Benzyl-3-[(2S,3R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyryl]-oxazolidin-2-one

Base Information

Chemical Name:(S)-4-Benzyl-3-[(2S,3R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyryl]-oxazolidin-2-one
CAS No.:819066-78-9
Molecular Formula:C₂₂H₃₁NO₆
Molecular Weight:405.491
Hs Code.:

Synonyms:(S)-4-Benzyl-3-[(2S,3R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyryl]-oxazolidin-2-one

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Chemical Property of (S)-4-Benzyl-3-[(2S,3R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyryl]-oxazolidin-2-one

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Technology Process of (S)-4-Benzyl-3-[(2S,3R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyryl]-oxazolidin-2-one

There total 1 articles about (S)-4-Benzyl-3-[(2S,3R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyryl]-oxazolidin-2-one 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: 95.0%

: 127793-59-3
(S)-(2,2-diethyl-[1,3]dioxan-4-yl)acetaldehyde

: 131685-53-5,101711-78-8
(S)-4-benzyl-3-propionyl-2-oxazolidinone

: 819066-78-9
(S)-4-Benzyl-3-[(2S,3R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyryl]-oxazolidin-2-one

Guidance literature:: With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/j.tetlet.2004.10.071

Reference yield:

: 819066-78-9
(S)-4-Benzyl-3-[(2S,3R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyryl]-oxazolidin-2-one

: 819066-90-5
(4aR,5S,7R,8aR)-7-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxine-5-carbaldehyde

Guidance literature:: Multi-step reaction with 15 steps

1: Dowex(R) / aq. methanol / 12 h / Heating

2: imidazole; 4-DMAP / CH₂Cl₂ / 1.5 h / 0 °C

3: LiOH*H₂O; aq. H₂O₂ / tetrahydrofuran / 1.5 h / 0 °C

4: EDC; HOBT; Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

5: 97 percent / 2,6-lutidine / dimethylformamide / 13 h / 20 °C

6: 97 percent / n-BuLi / tetrahydrofuran / 2 h / -78 °C

7: 51 percent / POCl₃ / pyridine / 48 h / 20 °C

8: n-Bu₄NF / tetrahydrofuran / 1 h / 20 °C

9: imidazole; 4-DMAP / CH₂Cl₂ / 2 h / 20 °C

10: 86 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 1 h / 20 °C

11: n-Bu₃SnCl; NaBH₃(CN); AIBN / 2-methyl-propan-2-ol / 3 h / 100 °C

12: KHCO₃; H₂O₂ / tetrahydrofuran; methanol / 1.5 h / 90 °C

13: 90 percent / PPTS / CH₂Cl₂ / 10 h / Heating

14: 77 percent / Li; NH₃ / tetrahydrofuran / 0.33 h / -78 °C

15: 85 percent / Dess-Martin periodinane / CH₂Cl₂

With 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium hydroxide; n-butyllithium; 2,2'-azobis(isobutyronitrile); Dowex(R); tributyltin chloride; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium; sodium cyanoborohydride; benzotriazol-1-ol; potassium hydrogencarbonate; Dess-Martin periodane; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trichlorophosphate; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 12: Tamao oxidation reaction;
DOI:10.1016/j.tetlet.2004.10.071

Reference yield:

: 819066-78-9
(S)-4-Benzyl-3-[(2S,3R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyryl]-oxazolidin-2-one

: 819066-91-6
(4aR,5R,7R,8aR)-7-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxine-5-carbaldehyde

Guidance literature:: Multi-step reaction with 16 steps

1: Dowex(R) / aq. methanol / 12 h / Heating

2: imidazole; 4-DMAP / CH₂Cl₂ / 1.5 h / 0 °C

3: LiOH*H₂O; aq. H₂O₂ / tetrahydrofuran / 1.5 h / 0 °C

4: EDC; HOBT; Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

5: 97 percent / 2,6-lutidine / dimethylformamide / 13 h / 20 °C

6: 97 percent / n-BuLi / tetrahydrofuran / 2 h / -78 °C

7: 51 percent / POCl₃ / pyridine / 48 h / 20 °C

8: n-Bu₄NF / tetrahydrofuran / 1 h / 20 °C

9: imidazole; 4-DMAP / CH₂Cl₂ / 2 h / 20 °C

10: 86 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 1 h / 20 °C

11: n-Bu₃SnCl; NaBH₃(CN); AIBN / 2-methyl-propan-2-ol / 3 h / 100 °C

12: KHCO₃; H₂O₂ / tetrahydrofuran; methanol / 1.5 h / 90 °C

13: 90 percent / PPTS / CH₂Cl₂ / 10 h / Heating

14: 77 percent / Li; NH₃ / tetrahydrofuran / 0.33 h / -78 °C

15: 85 percent / Dess-Martin periodinane / CH₂Cl₂

16: 46 percent / DBU / 0.5 h / 90 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium hydroxide; n-butyllithium; 2,2'-azobis(isobutyronitrile); Dowex(R); tributyltin chloride; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium; sodium cyanoborohydride; benzotriazol-1-ol; potassium hydrogencarbonate; Dess-Martin periodane; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trichlorophosphate; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 12: Tamao oxidation reaction;
DOI:10.1016/j.tetlet.2004.10.071