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

Base Information

Chemical Name:(3R,3aR,6aS)-tert-butyl 3-(2-hydroxyethyl)-1-(4-methoxybenzyl)-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrole-6a-carboxylate
CAS No.:856682-04-7
Molecular Formula:C₂₁H₂₇NO₇
Molecular Weight:405.448
Hs Code.:

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

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Chemical Property of (3R,3aR,6aS)-tert-butyl 3-(2-hydroxyethyl)-1-(4-methoxybenzyl)-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrole-6a-carboxylate

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Technology Process of (3R,3aR,6aS)-tert-butyl 3-(2-hydroxyethyl)-1-(4-methoxybenzyl)-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrole-6a-carboxylate

There total 19 articles about (3R,3aR,6aS)-tert-butyl 3-(2-hydroxyethyl)-1-(4-methoxybenzyl)-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrole-6a-carboxylate 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: 100.0%

: 856682-13-8
3-(2-benzyloxy-ethyl)-1-(4-methoxy-benzyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester

: 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

Guidance literature:: With hydrogen; palladium dihydroxide; In ethanol; for 16h; under 760 Torr;
DOI:10.1021/ja0522783

Reference yield: 88.0%

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

: 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

Guidance literature:: (3R,3aR,6aS)-tert-butyl 3-allyl-1-(4-methoxybenzyl)-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrole-6a-carboxylate; With oxygen; ozone; In methanol; dichloromethane; at -78 ℃;

With sodium tetrahydroborate; In methanol; dichloromethane; at -78 - 0 ℃; for 1h;
DOI:10.1021/ol501662t

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 11 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

With hydrogenchloride; 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