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

Base Information

• Chemical Name: 3-(2-benzyloxy-ethyl)-1-(4-methoxy-benzyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester
• CAS No.: 856682-13-8
• Molecular Formula: C₂₈H₃₃NO₇
• Molecular Weight: 495.573

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

Chemical Property of 3-(2-benzyloxy-ethyl)-1-(4-methoxy-benzyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 3-(2-benzyloxy-ethyl)-1-(4-methoxy-benzyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester

There total 12 articles about 3-(2-benzyloxy-ethyl)-1-(4-methoxy-benzyl)-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: 62.0%

3-(2-benzyloxy-ethyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester (856682-12-7) + p-methoxybenzyl chloride (824-94-2) → 3-(2-benzyloxy-ethyl)-1-(4-methoxy-benzyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester (856682-13-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/ja0522783

Reference yield:

(3S,7S,7aR)-3-Phenyl-7-vinyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one (856681-99-7) → 3-(2-benzyloxy-ethyl)-1-(4-methoxy-benzyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester (856682-13-8)

Guidance literature:

Multi-step reaction with 10 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

With hydrogenchloride; jones reagent; trifluorormethanesulfonic acid; sodium hydride; potassium carbonate; ozone; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 5.1: Jones' oxidation;

DOI:10.1021/ja0522783

Reference yield:

(3S,6R,7R,7aR)-6-(2-Benzyloxy-ethyl)-3-phenyl-7-vinyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one (856682-00-3) → 3-(2-benzyloxy-ethyl)-1-(4-methoxy-benzyl)-2,6-dioxo-tetrahydro-furo[3,4-b]pyrrole-6a-carboxylic acid tert-butyl ester (856682-13-8)

Guidance literature:

Multi-step reaction with 9 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

With hydrogenchloride; jones reagent; trifluorormethanesulfonic acid; sodium hydride; potassium carbonate; ozone; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 4.1: Jones' oxidation;

DOI:10.1021/ja0522783

upstream raw materials:

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

p-methoxybenzyl chloride

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

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

Downstream raw materials:

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

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

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

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

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