3-(2-benzyloxy-ethyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester

Base Information

Chemical Name:3-(2-benzyloxy-ethyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester
CAS No.:856682-12-7
Molecular Formula:C₂₀H₂₅NO₆
Molecular Weight:375.422
Hs Code.:

3-(2-benzyloxy-ethyl)-2,6-dioxo-tetrahydro-furo[3,4-<i>b</i>]pyrrole-6a-carboxylic acid <i>tert</i>-butyl ester

Synonyms:3-(2-benzyloxy-ethyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester

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Chemical Property of 3-(2-benzyloxy-ethyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester

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Technology Process of 3-(2-benzyloxy-ethyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester

There total 11 articles about 3-(2-benzyloxy-ethyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic 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: 90.0%

: 856682-03-6
3-(2-benzyloxy-ethyl)-2-ethoxy-6-oxo-3a,4-dihydro-3H-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester

: 856682-12-7
3-(2-benzyloxy-ethyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1021/ja0522783

Reference yield:

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

: 856682-12-7
3-(2-benzyloxy-ethyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 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

With hydrogenchloride; jones reagent; trifluorormethanesulfonic acid; potassium carbonate; ozone; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; 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

: 856682-12-7
3-(2-benzyloxy-ethyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 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

With hydrogenchloride; jones reagent; trifluorormethanesulfonic acid; potassium carbonate; ozone; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetone; toluene; 4.1: Jones' oxidation;
DOI:10.1021/ja0522783