[(3aS,5aR,8aS,8bR)-3-Ethoxycarbonylmethyl-3,3a,5a,6,7,8,8a,8b-octahydro-indeno[4,5-c]furan-(1E)-ylidene]-acetic acid benzyl ester

Base Information

Chemical Name:[(3aS,5aR,8aS,8bR)-3-Ethoxycarbonylmethyl-3,3a,5a,6,7,8,8a,8b-octahydro-indeno[4,5-c]furan-(1E)-ylidene]-acetic acid benzyl ester
CAS No.:130953-64-9
Molecular Formula:C₂₄H₂₈O₅
Molecular Weight:396.483
Hs Code.:

Synonyms:

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Chemical Property of [(3aS,5aR,8aS,8bR)-3-Ethoxycarbonylmethyl-3,3a,5a,6,7,8,8a,8b-octahydro-indeno[4,5-c]furan-(1E)-ylidene]-acetic acid benzyl ester

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Technology Process of [(3aS,5aR,8aS,8bR)-3-Ethoxycarbonylmethyl-3,3a,5a,6,7,8,8a,8b-octahydro-indeno[4,5-c]furan-(1E)-ylidene]-acetic acid benzyl ester

There total 10 articles about [(3aS,5aR,8aS,8bR)-3-Ethoxycarbonylmethyl-3,3a,5a,6,7,8,8a,8b-octahydro-indeno[4,5-c]furan-(1E)-ylidene]-acetic acid benzyl 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:

: 76102-74-4
5-(tetrahydro-2H-pyran-2-yloxy)pentan-1-ol

: 130953-64-9
[(3aS,5aR,8aS,8bR)-3-Ethoxycarbonylmethyl-3,3a,5a,6,7,8,8a,8b-octahydro-indeno[4,5-c]furan-(1E)-ylidene]-acetic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 78 percent / PCC, NaOAc

2: 1) n-BuLi / THF, -78 deg C

3: LiAlH₄

4: p-TsOH, H₂O / tetrahydrofuran

5: 73 percent / toluene / Heating

6: 90 percent / MeOH, Amberlite 15

7: 61 percent / PCC, NaOAc

8: 81 percent / aq. K₂CO₃ / 20 °C

9: 67 percent / toluene / Heating

10: 1) LDA, HMPA / THF, 1) -78 deg C, 2) -78 deg C, 10 min

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; Amberlite 15; water; sodium acetate; potassium carbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; toluene;
DOI:10.1016/S0040-4039(00)89066-8

Reference yield:

: 14194-86-6
5-(2-tetrahydropyranyloxy)pentanal

: 130953-64-9
[(3aS,5aR,8aS,8bR)-3-Ethoxycarbonylmethyl-3,3a,5a,6,7,8,8a,8b-octahydro-indeno[4,5-c]furan-(1E)-ylidene]-acetic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 1) n-BuLi / THF, -78 deg C

2: LiAlH₄

3: p-TsOH, H₂O / tetrahydrofuran

4: 73 percent / toluene / Heating

5: 90 percent / MeOH, Amberlite 15

6: 61 percent / PCC, NaOAc

7: 81 percent / aq. K₂CO₃ / 20 °C

8: 67 percent / toluene / Heating

9: 1) LDA, HMPA / THF, 1) -78 deg C, 2) -78 deg C, 10 min

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; Amberlite 15; water; sodium acetate; potassium carbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; toluene;
DOI:10.1016/S0040-4039(00)89066-8

Reference yield:

: 111-29-5
1 ,5-pentanediol

: 130953-64-9
[(3aS,5aR,8aS,8bR)-3-Ethoxycarbonylmethyl-3,3a,5a,6,7,8,8a,8b-octahydro-indeno[4,5-c]furan-(1E)-ylidene]-acetic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 60 percent / PPTS

2: 78 percent / PCC, NaOAc

3: 1) n-BuLi / THF, -78 deg C

4: LiAlH₄

5: p-TsOH, H₂O / tetrahydrofuran

6: 73 percent / toluene / Heating

7: 90 percent / MeOH, Amberlite 15

8: 61 percent / PCC, NaOAc

9: 81 percent / aq. K₂CO₃ / 20 °C

10: 67 percent / toluene / Heating

11: 1) LDA, HMPA / THF, 1) -78 deg C, 2) -78 deg C, 10 min

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; Amberlite 15; water; sodium acetate; pyridinium p-toluenesulfonate; potassium carbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; toluene;
DOI:10.1016/S0040-4039(00)89066-8