(3aS,6S,6aR)-(9H-fluoren-9-yl)methyl 6-benzyl-3-oxotetrahydro-2H-furo[3.2-b]pyrrole-4(5H)-carboxylate

Base Information

• Chemical Name: (3aS,6S,6aR)-(9H-fluoren-9-yl)methyl 6-benzyl-3-oxotetrahydro-2H-furo[3.2-b]pyrrole-4(5H)-carboxylate
• CAS No.: 1172140-59-8
• Molecular Formula: C₂₈H₂₅NO₄
• Molecular Weight: 439.511
• Mol file: 1172140-59-8.mol

Synonyms:(3aS,6S,6aR)-(9H-fluoren-9-yl)methyl 6-benzyl-3-oxotetrahydro-2H-furo[3.2-b]pyrrole-4(5H)-carboxylate

Chemical Property of (3aS,6S,6aR)-(9H-fluoren-9-yl)methyl 6-benzyl-3-oxotetrahydro-2H-furo[3.2-b]pyrrole-4(5H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,6S,6aR)-(9H-fluoren-9-yl)methyl 6-benzyl-3-oxotetrahydro-2H-furo[3.2-b]pyrrole-4(5H)-carboxylate

There total 13 articles about (3aS,6S,6aR)-(9H-fluoren-9-yl)methyl 6-benzyl-3-oxotetrahydro-2H-furo[3.2-b]pyrrole-4(5H)-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: 93.0%

(3R,3aR,6S,6aR)-(9H-fluoren-9-yl)methyl 6-benzyl-3-hydroxytetrahydro-2H-furo[3.2-b]pyrrole-4(5H)-carboxylate (1172140-57-6) → (3aS,6S,6aR)-(9H-fluoren-9-yl)methyl 6-benzyl-3-oxotetrahydro-2H-furo[3.2-b]pyrrole-4(5H)-carboxylate (1172140-59-8)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 2h; Inert atmosphere;

Reference yield:

(3R,6R)-hexahydrofuro[3,2-b]furan-3,6-diol → (3aS,6S,6aR)-(9H-fluoren-9-yl)methyl 6-benzyl-3-oxotetrahydro-2H-furo[3.2-b]pyrrole-4(5H)-carboxylate (1172140-59-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: potassium hydroxide / tetrachloromethane; dichloromethane; water / 26 h / 0 °C / Inert atmosphere

2.1: lithium bromide / N,N-dimethyl-formamide / 27 h / 100 °C

3.1: water; ammonium chloride; zinc / tetrahydrofuran; isopropyl alcohol / 16 h / Inert atmosphere

4.1: ammonium hydroxide; ammonia; water / isopropyl alcohol / 16 h / 75 °C

5.1: sodium carbonate / 1,4-dioxane; water / 1.58 h / 0 °C

6.1: pyridine / 22 h / 24 - 40 °C

7.1: Oxone; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate / water; acetonitrile / 0 °C

8.1: hydrogen / palladium 10% on activated carbon / ethanol / 1.5 h

9.1: lithium chloride; copper(I) bromide / tetrahydrofuran; diethyl ether / 1.83 h / -50 - -45 °C

9.2: 8 °C

9.3: 0.33 h

10.1: sodium carbonate / 1,4-dioxane; water / 0 °C

11.1: Dess-Martin periodane / dichloromethane / 2 h / Inert atmosphere

With pyridine; Oxone; ammonium hydroxide; 1,1,1-trifluoro-2-propanone; ammonia; water; hydrogen; sodium hydrogencarbonate; sodium carbonate; ammonium chloride; Dess-Martin periodane; lithium chloride; potassium hydroxide; copper(I) bromide; lithium bromide; zinc; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

Reference yield:

(S)-2-(benzyloxycarbonylamino)-1-((1S,2S,5S)-3,6-dioxabicyclo[3.1.0]hexan-2-yl)ethyl 4-methylbenzenesulphonate → (3aS,6S,6aR)-(9H-fluoren-9-yl)methyl 6-benzyl-3-oxotetrahydro-2H-furo[3.2-b]pyrrole-4(5H)-carboxylate (1172140-59-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogen / palladium 10% on activated carbon / ethanol / 1.5 h

2.1: lithium chloride; copper(I) bromide / tetrahydrofuran; diethyl ether / 1.83 h / -50 - -45 °C

2.2: 8 °C

2.3: 0.33 h

3.1: sodium carbonate / 1,4-dioxane; water / 0 °C

4.1: Dess-Martin periodane / dichloromethane / 2 h / Inert atmosphere

With hydrogen; sodium carbonate; Dess-Martin periodane; lithium chloride; copper(I) bromide; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; water;

upstream raw materials:

(3R,3aR,6S,6aR)-(9H-fluoren-9-yl)methyl 6-benzyl-3-hydroxytetrahydro-2H-furo[3.2-b]pyrrole-4(5H)-carboxylate

(3R,3aR,6S,6aS)-3-hydroxyhexahydro-2H-furo[3,2-b]pyrrol-6-yl 4-methylbenzenesulfonate

(R)-1-((S)-2,5-dihydrofuran-2-yl)-2-hydroxyethyl 4-methyl-benzenesulfonate

benzyl (S)-2-((S)-2,5-dihydrofuran-2-yl)-2-hydroxyethylcarbamate