(3aR,7S,8aR,Z)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-7-methyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one

Base Information

• Chemical Name: (3aR,7S,8aR,Z)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-7-methyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one
• CAS No.: 935733-55-4
• Molecular Formula: C₂₈H₃₆O₃Si
• Molecular Weight: 448.678
• Mol file: 935733-55-4.mol

Synonyms:(3aR,7S,8aR,Z)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-7-methyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one

Chemical Property of (3aR,7S,8aR,Z)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-7-methyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,7S,8aR,Z)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-7-methyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one

There total 36 articles about (3aR,7S,8aR,Z)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-7-methyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one 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:

6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-7-methyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-ol (935733-59-8) → (3aR,7S,8aR,Z)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-7-methyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one (935733-55-4)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ol062960h

Reference yield:

(2R,3S)-3-hydroxy-N-methoxy-N,2-dimethylhept-6-enamide (779338-01-1) → (3aR,7S,8aR,Z)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-7-methyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one (935733-55-4)

Guidance literature:

Multi-step reaction with 16 steps

1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

2: 92 percent / tetrahydrofuran / 1 h / 0 °C

3: 95 percent / 2-nd generation Grubbs' catalyst / CH₂Cl₂ / 4 h / Heating

4: 74 percent / Red-Al(R) / diethyl ether; toluene / 1.5 h / -78 °C

5: 96 percent / toluene / 30 h / Heating

6: 89 percent / I₂ / tetrahydrofuran; H₂O / 12 h / 20 °C

7: 100 percent / Bu₃SnH / benzene / 1 h / Heating

8: DIBAL-H / tetrahydrofuran / 1 h / -78 °C

9: TsOH*H₂O / 1.5 h / Heating

10: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

11: 99 percent / Li(O-Hex)2 / tetrahydrofuran / 3 h / -78 - -25 °C

12: 36 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

13: 93 percent / DIBAL-H / tetrahydrofuran / 1 h / -78 °C

14: imidazole; DMAP / CH₂Cl₂ / 0.5 h / 20 °C

15: AcOH / acetone; H₂O / 20 h / 20 °C

16: 67.4 mg / NMO; TPAP / CH₂Cl₂ / 1 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; Li(O-Hex)2; iodine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; toluene; benzene; 11: Peterson olefination;

DOI:10.1021/ol062960h

Reference yield:

3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-hept-6-enoic acid methoxy-methyl-amide (935733-57-6) → (3aR,7S,8aR,Z)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-7-methyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one (935733-55-4)

Guidance literature:

Multi-step reaction with 15 steps

1: 92 percent / tetrahydrofuran / 1 h / 0 °C

2: 95 percent / 2-nd generation Grubbs' catalyst / CH₂Cl₂ / 4 h / Heating

3: 74 percent / Red-Al(R) / diethyl ether; toluene / 1.5 h / -78 °C

4: 96 percent / toluene / 30 h / Heating

5: 89 percent / I₂ / tetrahydrofuran; H₂O / 12 h / 20 °C

6: 100 percent / Bu₃SnH / benzene / 1 h / Heating

7: DIBAL-H / tetrahydrofuran / 1 h / -78 °C

8: TsOH*H₂O / 1.5 h / Heating

9: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

10: 99 percent / Li(O-Hex)2 / tetrahydrofuran / 3 h / -78 - -25 °C

11: 36 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

12: 93 percent / DIBAL-H / tetrahydrofuran / 1 h / -78 °C

13: imidazole; DMAP / CH₂Cl₂ / 0.5 h / 20 °C

14: AcOH / acetone; H₂O / 20 h / 20 °C

15: 67.4 mg / NMO; TPAP / CH₂Cl₂ / 1 h / 20 °C

With 1H-imidazole; dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; Li(O-Hex)2; iodine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; toluene; benzene; 10: Peterson olefination;

DOI:10.1021/ol062960h

upstream raw materials:

6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-7-methyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-ol

(2R,3S)-3-hydroxy-N-methoxy-N,2-dimethylhept-6-enamide

(3aR,7S,8aR)-2-methoxy-7-methylhexahydro-2H-cyclohepta[b]furan-6(7H)-one

(3aR,6S,7S,8aR)-2-methoxy-7-methyloctahydro-2H-cyclohepta[b]furan-2-ol

Downstream raw materials:

(3R,3aR,7S,8aR,Z)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-3,7-dimethyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one