(2S,3R,4R)-4-(2-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-5-oxo-3-phenylselanylmethyl-pyrrolidine-2,2-dicarboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,3R,4R)-4-(2-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-5-oxo-3-phenylselanylmethyl-pyrrolidine-2,2-dicarboxylic acid tert-butyl ester
CAS No.:915315-28-5
Molecular Formula:C₂₇H₃₃NO₇Se
Molecular Weight:562.522
Hs Code.:

Synonyms:(2S,3R,4R)-4-(2-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-5-oxo-3-phenylselanylmethyl-pyrrolidine-2,2-dicarboxylic acid tert-butyl ester

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Chemical Property of (2S,3R,4R)-4-(2-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-5-oxo-3-phenylselanylmethyl-pyrrolidine-2,2-dicarboxylic acid tert-butyl ester

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Technology Process of (2S,3R,4R)-4-(2-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-5-oxo-3-phenylselanylmethyl-pyrrolidine-2,2-dicarboxylic acid tert-butyl ester

There total 13 articles about (2S,3R,4R)-4-(2-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-5-oxo-3-phenylselanylmethyl-pyrrolidine-2,2-dicarboxylic acid tert-butyl ester 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:

: 856682-04-7
(3R,3aR,6aS)-tert-butyl 3-(2-hydroxyethyl)-1-(4-methoxybenzyl)-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrole-6a-carboxylate

: 1666-13-3
diphenyl diselenide

: 915315-28-5
(2S,3R,4R)-4-(2-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-5-oxo-3-phenylselanylmethyl-pyrrolidine-2,2-dicarboxylic acid tert-butyl ester

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 20 - 60 ℃; for 4h;
DOI:10.1021/ja0522783

Reference yield:

: 856681-99-7
(3S,7S,7aR)-3-Phenyl-7-vinyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

: 915315-28-5
(2S,3R,4R)-4-(2-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-5-oxo-3-phenylselanylmethyl-pyrrolidine-2,2-dicarboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: LDA / tetrahydrofuran; hexane / 1 h / 0 °C

1.2: 77 percent / tetrahydrofuran; hexane / 0 - 20 °C

2.1: O₃ / CH₂Cl₂; methanol / -78 °C

2.2: 86 percent / NaBH₄ / tetrahydrofuran; methanol / -78 - 0 °C

3.1: 96 percent / pyridine / 0 - 20 °C

4.1: 100 percent / TfOH / tetrahydrofuran; H₂O / 18 h / 20 °C

5.1: Jones reagent / acetone / 0 - 20 °C

6.1: 10.08 g / toluene / 1 h / Heating

7.1: 88 percent / K₂CO₃ / CH₂Cl₂ / 0 - 20 °C

8.1: 82 percent / LHMDS / tetrahydrofuran / 0.17 h / -20 °C

9.1: 90 percent / aq. HCl / tetrahydrofuran / 1 h / 0 °C

10.1: 62 percent / NaH / dimethylformamide / 0 - 20 °C

11.1: 100 percent / H₂ / Pd(OH)2/C / ethanol / 16 h / 760 Torr

12.1: NaBH₄ / ethanol / 4 h / 20 - 60 °C

With hydrogenchloride; sodium tetrahydroborate; jones reagent; trifluorormethanesulfonic acid; hydrogen; sodium hydride; potassium carbonate; ozone; lithium hexamethyldisilazane; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 5.1: Jones' oxidation;
DOI:10.1021/ja0522783

Reference yield:

: 856682-00-3
(3S,6R,7R,7aR)-6-(2-Benzyloxy-ethyl)-3-phenyl-7-vinyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

: 915315-28-5
(2S,3R,4R)-4-(2-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-5-oxo-3-phenylselanylmethyl-pyrrolidine-2,2-dicarboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: O₃ / CH₂Cl₂; methanol / -78 °C

1.2: 86 percent / NaBH₄ / tetrahydrofuran; methanol / -78 - 0 °C

2.1: 96 percent / pyridine / 0 - 20 °C

3.1: 100 percent / TfOH / tetrahydrofuran; H₂O / 18 h / 20 °C

4.1: Jones reagent / acetone / 0 - 20 °C

5.1: 10.08 g / toluene / 1 h / Heating

6.1: 88 percent / K₂CO₃ / CH₂Cl₂ / 0 - 20 °C

7.1: 82 percent / LHMDS / tetrahydrofuran / 0.17 h / -20 °C

8.1: 90 percent / aq. HCl / tetrahydrofuran / 1 h / 0 °C

9.1: 62 percent / NaH / dimethylformamide / 0 - 20 °C

10.1: 100 percent / H₂ / Pd(OH)2/C / ethanol / 16 h / 760 Torr

11.1: NaBH₄ / ethanol / 4 h / 20 - 60 °C

With hydrogenchloride; sodium tetrahydroborate; jones reagent; trifluorormethanesulfonic acid; hydrogen; sodium hydride; potassium carbonate; ozone; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 4.1: Jones' oxidation;
DOI:10.1021/ja0522783