(4R,5S)-3-benzyl 4-methyl 5-((R)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-oxopyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate

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Chemical Name:(4R,5S)-3-benzyl 4-methyl 5-((R)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-oxopyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate
CAS No.:866331-60-4
Molecular Formula:C₂₆H₃₄N₂O₁₀
Molecular Weight:534.563
Hs Code.:

Synonyms:(4R,5S)-3-benzyl 4-methyl 5-((R)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-oxopyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate

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Chemical Property of (4R,5S)-3-benzyl 4-methyl 5-((R)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-oxopyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate

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Technology Process of (4R,5S)-3-benzyl 4-methyl 5-((R)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-oxopyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate

There total 16 articles about (4R,5S)-3-benzyl 4-methyl 5-((R)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-oxopyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate 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:

: (S)-3-Amino-6-oxo-tetrahydro-pyran-3-carboxylic acid methyl ester

: 866331-60-4
(4R,5S)-3-benzyl 4-methyl 5-((R)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-oxopyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate

Guidance literature:: Multi-step reaction with 15 steps

1: NaCN / methanol / 18 h / Heating

2: Et₃N; DMAP / CH₂Cl₂ / 20 h / 20 °C

3: 12.3 g / Et₃N; DMAP / tetrahydrofuran / 15 h / 20 °C

4: 93 percent / TBAF; AcOH / tetrahydrofuran / 22 h / 20 °C

5: 98 percent / TEMPO; PhI(OAc)2 / CH₂Cl₂ / 26 h / 20 °C

6: 98 percent / toluene / 1.5 h / 80 °C

7: 98 percent / OsO₄; DMAP / tetrahydrofuran / 19 h / -78 °C

8: 99 percent / CH₂Cl₂ / 2 h / Heating

9: TFA / CH₂Cl₂ / 1.5 h / 0 °C

10: 846 mg / NaN₃; PPTS / pentane / 16 h / 20 °C

11: 30 percent / CSA / toluene / 18 h / Heating

12: H₂ / Pd/C / ethyl acetate / 2.5 h / 20 °C

13: 57 mg / DMAP / CH₂Cl₂ / 21 h / 20 °C

14: TFA / CH₂Cl₂ / 3 h / 20 °C

15: 21 mg / DMAP / tetrahydrofuran / 15 h / 20 °C

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; osmium(VIII) oxide; sodium azide; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid; sodium cyanide; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; acetic acid; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; pentane; 6: Wittig reaction;
DOI:10.1021/ol0515154

Reference yield:

: 866331-50-2
(R)-2-Hydroxymethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

: 866331-60-4
(4R,5S)-3-benzyl 4-methyl 5-((R)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-oxopyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate

Guidance literature:: Multi-step reaction with 14 steps

1: Et₃N; DMAP / CH₂Cl₂ / 20 h / 20 °C

2: 12.3 g / Et₃N; DMAP / tetrahydrofuran / 15 h / 20 °C

3: 93 percent / TBAF; AcOH / tetrahydrofuran / 22 h / 20 °C

4: 98 percent / TEMPO; PhI(OAc)2 / CH₂Cl₂ / 26 h / 20 °C

5: 98 percent / toluene / 1.5 h / 80 °C

6: 98 percent / OsO₄; DMAP / tetrahydrofuran / 19 h / -78 °C

7: 99 percent / CH₂Cl₂ / 2 h / Heating

8: TFA / CH₂Cl₂ / 1.5 h / 0 °C

9: 846 mg / NaN₃; PPTS / pentane / 16 h / 20 °C

10: 30 percent / CSA / toluene / 18 h / Heating

11: H₂ / Pd/C / ethyl acetate / 2.5 h / 20 °C

12: 57 mg / DMAP / CH₂Cl₂ / 21 h / 20 °C

13: TFA / CH₂Cl₂ / 3 h / 20 °C

14: 21 mg / DMAP / tetrahydrofuran / 15 h / 20 °C

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; osmium(VIII) oxide; sodium azide; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; acetic acid; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; pentane; 5: Wittig reaction;
DOI:10.1021/ol0515154

Reference yield:

: 866331-49-9
(2R)-1-tert-butyl 2-formyl-5-oxopyrrolidine-1,2-dicarboxylate methyl ester

: 866331-60-4
(4R,5S)-3-benzyl 4-methyl 5-((R)-1-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-5-oxopyrrolidin-2-yl)-2,2-dimethyloxazolidine-3,4-dicarboxylate

Guidance literature:: Multi-step reaction with 10 steps

1: 98 percent / toluene / 1.5 h / 80 °C

2: 98 percent / OsO₄; DMAP / tetrahydrofuran / 19 h / -78 °C

3: 99 percent / CH₂Cl₂ / 2 h / Heating

4: TFA / CH₂Cl₂ / 1.5 h / 0 °C

5: 846 mg / NaN₃; PPTS / pentane / 16 h / 20 °C

6: 30 percent / CSA / toluene / 18 h / Heating

7: H₂ / Pd/C / ethyl acetate / 2.5 h / 20 °C

8: 57 mg / DMAP / CH₂Cl₂ / 21 h / 20 °C

9: TFA / CH₂Cl₂ / 3 h / 20 °C

10: 21 mg / DMAP / tetrahydrofuran / 15 h / 20 °C

With dmap; osmium(VIII) oxide; sodium azide; camphor-10-sulfonic acid; hydrogen; pyridinium p-toluenesulfonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; pentane; 1: Wittig reaction;
DOI:10.1021/ol0515154