Furo[2,3-b]pyridine-7(4H)-carboxylic acid, hexahydro-4-oxo-5-phenyl-3a,5-bis(phenylseleno)-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: Furo[2,3-b]pyridine-7(4H)-carboxylic acid, hexahydro-4-oxo-5-phenyl-3a,5-bis(phenylseleno)-, 1,1-dimethylethyl ester
• CAS No.: 677325-05-2
• Molecular Formula: C30H31NO4Se2
• Molecular Weight: 627.5
• Mol file: 677325-05-2.mol

Synonyms:

Chemical Property of Furo[2,3-b]pyridine-7(4H)-carboxylic acid, hexahydro-4-oxo-5-phenyl-3a,5-bis(phenylseleno)-, 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Furo[2,3-b]pyridine-7(4H)-carboxylic acid, hexahydro-4-oxo-5-phenyl-3a,5-bis(phenylseleno)-, 1,1-dimethylethyl ester

There total 11 articles about Furo[2,3-b]pyridine-7(4H)-carboxylic acid, hexahydro-4-oxo-5-phenyl-3a,5-bis(phenylseleno)-, 1,1-dimethylethyl 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:

3-((tert-butyldimethylsilyl)oxy)-2-phenylpropan-1-ol (173423-55-7) → hexahydro-4-oxo-5-phenyl-3a,5-bis(phenylselanyl)furo[2,3-b]pyridine-7-carboxylic acid tert-butyl ester (677325-05-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 91 percent / PPh₃; DEAD / tetrahydrofuran / 5 h / 0 °C

2: 97 percent / H₂NNH₂*H₂O / ethanol / 2 h / 80 °C

3: 100 percent / NaHCO₃ / acetone; H₂O / 12 h

4: 74 percent / Bu₄NF / tetrahydrofuran / 0.17 h / 0 °C

5: 93 percent / Dess-Martin reagent / CH₂Cl₂ / 1 h

6: BuLi; i-Pr₂NH / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1.33 h / -78 °C

7: DIBALH / toluene; CH₂Cl₂ / 0.67 h / -78 °C

8: TsOH*pyridine / tetrahydrofuran / 1 h

9: 82 percent / Dess-Martin reagent / CH₂Cl₂ / 1 h

10: 62 percent / (Me₃Si)2NK / toluene; tetrahydrofuran / -78 - 0 °C

With n-butyllithium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; hydrazine hydrate; diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; dichloromethane; water; acetone; toluene; 1: Mitsunobu reaction / 5: Dess-Martin oxidation / 9: Dess-Martin oxidation;

DOI:10.1021/jo030284g

Reference yield:

2-[3-[(tert-butyldimethylsilanyl)oxy]-2-phenylpropyl]isoindole-2,3-dione (618094-94-3) → hexahydro-4-oxo-5-phenyl-3a,5-bis(phenylselanyl)furo[2,3-b]pyridine-7-carboxylic acid tert-butyl ester (677325-05-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 97 percent / H₂NNH₂*H₂O / ethanol / 2 h / 80 °C

2: 100 percent / NaHCO₃ / acetone; H₂O / 12 h

3: 74 percent / Bu₄NF / tetrahydrofuran / 0.17 h / 0 °C

4: 93 percent / Dess-Martin reagent / CH₂Cl₂ / 1 h

5: BuLi; i-Pr₂NH / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1.33 h / -78 °C

6: DIBALH / toluene; CH₂Cl₂ / 0.67 h / -78 °C

7: TsOH*pyridine / tetrahydrofuran / 1 h

8: 82 percent / Dess-Martin reagent / CH₂Cl₂ / 1 h

9: 62 percent / (Me₃Si)2NK / toluene; tetrahydrofuran / -78 - 0 °C

With n-butyllithium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; hydrazine hydrate; diisopropylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; dichloromethane; water; acetone; toluene; 4: Dess-Martin oxidation / 8: Dess-Martin oxidation;

DOI:10.1021/jo030284g

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → hexahydro-4-oxo-5-phenyl-3a,5-bis(phenylselanyl)furo[2,3-b]pyridine-7-carboxylic acid tert-butyl ester (677325-05-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.600 g / NaHCO₃ / acetone; H₂O / 4 h

2: 93 percent / Dess-Martin reagent / CH₂Cl₂ / 1 h

3: BuLi; i-Pr₂NH / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1.33 h / -78 °C

4: DIBALH / toluene; CH₂Cl₂ / 0.67 h / -78 °C

5: TsOH*pyridine / tetrahydrofuran / 1 h

6: 82 percent / Dess-Martin reagent / CH₂Cl₂ / 1 h

7: 62 percent / (Me₃Si)2NK / toluene; tetrahydrofuran / -78 - 0 °C

With n-butyllithium; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; diisopropylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water; acetone; toluene; 2: Dess-Martin oxidation / 6: Dess-Martin oxidation;

DOI:10.1021/jo030284g

upstream raw materials:

di-tert-butyl dicarbonate

3-Hydroxy-2-phenyl-1-aminopropane

(3-oxo-2-phenylpropyl)carbamic acid tert-butyl ester

(3-hydroxy-2-phenylpropyl)carbamic acid tert-butyl ester