2-benzyloxy-4-ethoxy-6-formyl-6a-methyl-3,3a,6,6a-tetrahydro-2H-furo[2,3-c]pyrrole-6-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 2-benzyloxy-4-ethoxy-6-formyl-6a-methyl-3,3a,6,6a-tetrahydro-2H-furo[2,3-c]pyrrole-6-carboxylic acid tert-butyl ester
• CAS No.: 856682-27-4
• Molecular Formula: C₂₂H₂₉NO₆
• Molecular Weight: 403.475

Synonyms:2-benzyloxy-4-ethoxy-6-formyl-6a-methyl-3,3a,6,6a-tetrahydro-2H-furo[2,3-c]pyrrole-6-carboxylic acid tert-butyl ester

Chemical Property of 2-benzyloxy-4-ethoxy-6-formyl-6a-methyl-3,3a,6,6a-tetrahydro-2H-furo[2,3-c]pyrrole-6-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of 2-benzyloxy-4-ethoxy-6-formyl-6a-methyl-3,3a,6,6a-tetrahydro-2H-furo[2,3-c]pyrrole-6-carboxylic acid tert-butyl ester

There total 19 articles about 2-benzyloxy-4-ethoxy-6-formyl-6a-methyl-3,3a,6,6a-tetrahydro-2H-furo[2,3-c]pyrrole-6-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:

(3S,7S,7aR)-3-Phenyl-7-vinyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one (856681-99-7) → 2-benzyloxy-4-ethoxy-6-formyl-6a-methyl-3,3a,6,6a-tetrahydro-2H-furo[2,3-c]pyrrole-6-carboxylic acid tert-butyl ester (856682-27-4)

Guidance literature:

Multi-step reaction with 18 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: 97 percent / H₂ / Pd(OH)2/C / ethanol; ethyl acetate / 20 °C

11.1: NaBH₄ / ethanol / 60 °C

12.1: K₂CO₃ / dimethylformamide / 20 °C

13.1: aq. H₂O₂ / tetrahydrofuran; toluene / Heating

13.2: Dess- Martin periodinane / CH₂Cl₂ / 20 °C

14.1: AgBF₄ / CH₂Cl₂ / 0 °C

15.1: 100 percent / Bu₃SnH; AIBN / toluene / Heating

16.1: 84 percent / NaBH₄ / tetrahydrofuran; ethanol / 20 °C

17.1: K₂CO₃ / CH₂Cl₂ / 20 °C

With hydrogenchloride; sodium tetrahydroborate; silver tetrafluoroborate; jones reagent; 2,2'-azobis(isobutyronitrile); trifluorormethanesulfonic acid; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; potassium carbonate; ozone; lithium hexamethyldisilazane; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; 5.1: Jones' oxidation / 18.1: Swern 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) → 2-benzyloxy-4-ethoxy-6-formyl-6a-methyl-3,3a,6,6a-tetrahydro-2H-furo[2,3-c]pyrrole-6-carboxylic acid tert-butyl ester (856682-27-4)

Guidance literature:

Multi-step reaction with 17 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: 97 percent / H₂ / Pd(OH)2/C / ethanol; ethyl acetate / 20 °C

10.1: NaBH₄ / ethanol / 60 °C

11.1: K₂CO₃ / dimethylformamide / 20 °C

12.1: aq. H₂O₂ / tetrahydrofuran; toluene / Heating

12.2: Dess- Martin periodinane / CH₂Cl₂ / 20 °C

13.1: AgBF₄ / CH₂Cl₂ / 0 °C

14.1: 100 percent / Bu₃SnH; AIBN / toluene / Heating

15.1: 84 percent / NaBH₄ / tetrahydrofuran; ethanol / 20 °C

16.1: K₂CO₃ / CH₂Cl₂ / 20 °C

With hydrogenchloride; sodium tetrahydroborate; silver tetrafluoroborate; jones reagent; 2,2'-azobis(isobutyronitrile); trifluorormethanesulfonic acid; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; potassium carbonate; ozone; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; 4.1: Jones' oxidation / 17.1: Swern oxidation;

DOI:10.1021/ja0522783

Reference yield:

Carbonic acid (2R,3R,4R)-4-(2-benzyloxy-ethyl)-2-hydroxymethyl-5-oxo-pyrrolidin-3-ylmethyl ester ethyl ester (856682-02-5) → 2-benzyloxy-4-ethoxy-6-formyl-6a-methyl-3,3a,6,6a-tetrahydro-2H-furo[2,3-c]pyrrole-6-carboxylic acid tert-butyl ester (856682-27-4)

Guidance literature:

Multi-step reaction with 14 steps

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

2.1: 10.08 g / toluene / 1 h / Heating

3.1: 88 percent / K₂CO₃ / CH₂Cl₂ / 0 - 20 °C

4.1: 82 percent / LHMDS / tetrahydrofuran / 0.17 h / -20 °C

5.1: 90 percent / aq. HCl / tetrahydrofuran / 1 h / 0 °C

6.1: 97 percent / H₂ / Pd(OH)2/C / ethanol; ethyl acetate / 20 °C

7.1: NaBH₄ / ethanol / 60 °C

8.1: K₂CO₃ / dimethylformamide / 20 °C

9.1: aq. H₂O₂ / tetrahydrofuran; toluene / Heating

9.2: Dess- Martin periodinane / CH₂Cl₂ / 20 °C

10.1: AgBF₄ / CH₂Cl₂ / 0 °C

11.1: 100 percent / Bu₃SnH; AIBN / toluene / Heating

12.1: 84 percent / NaBH₄ / tetrahydrofuran; ethanol / 20 °C

13.1: K₂CO₃ / CH₂Cl₂ / 20 °C

With hydrogenchloride; sodium tetrahydroborate; silver tetrafluoroborate; jones reagent; 2,2'-azobis(isobutyronitrile); hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; potassium carbonate; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; 1.1: Jones' oxidation / 14.1: Swern oxidation;

DOI:10.1021/ja0522783

upstream raw materials:

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

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

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

Carbonic acid (2R,3R,4R)-4-(2-benzyloxy-ethyl)-2-hydroxymethyl-5-oxo-pyrrolidin-3-ylmethyl ester ethyl ester

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