(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

Base Information

Chemical Name:(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
CAS No.:935733-56-5
Molecular Formula:C₂₉H₃₈O₃Si
Molecular Weight:462.704
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 38 articles about (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 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: 100.0%

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

: 74-88-4
methyl iodide

: 935733-56-5
(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

Guidance literature:: (3aR,7S,8aR,Z)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]-7-methyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one; With 2,2,6,6-tetramethyl-piperidine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; hexane; at -78 - -40 ℃; for 12h; Inert atmosphere;
DOI:10.1021/ol201273b

Reference yield: 100.0%

: 225518-67-2
(3R,3aR,7S,8aR,Z)-6-(2-hydroxyethyl)-3,7-dimethyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one

: 58479-61-1
tert-butylchlorodiphenylsilane

: 935733-56-5
(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

Guidance literature:: With 1H-imidazole; dmap; In dichloromethane;
DOI:10.1016/j.tetlet.2008.04.141

Reference yield:

: 779338-01-1
(2R,3S)-3-hydroxy-N-methoxy-N,2-dimethylhept-6-enamide

: 935733-56-5
(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

Guidance literature:: Multi-step reaction with 17 steps

1.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

2.1: 92 percent / tetrahydrofuran / 1 h / 0 °C

3.1: 95 percent / 2-nd generation Grubbs' catalyst / CH₂Cl₂ / 4 h / Heating

4.1: 74 percent / Red-Al(R) / diethyl ether; toluene / 1.5 h / -78 °C

5.1: 96 percent / toluene / 30 h / Heating

6.1: 89 percent / I₂ / tetrahydrofuran; H₂O / 12 h / 20 °C

7.1: 100 percent / Bu₃SnH / benzene / 1 h / Heating

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

9.1: TsOH*H₂O / 1.5 h / Heating

10.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

11.1: 99 percent / Li(O-Hex)2 / tetrahydrofuran / 3 h / -78 - -25 °C

12.1: 36 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

13.1: 93 percent / DIBAL-H / tetrahydrofuran / 1 h / -78 °C

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

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

16.1: 67.4 mg / NMO; TPAP / CH₂Cl₂ / 1 h / 20 °C

17.1: lithium tetramethylpiperidide; HMPA / tetrahydrofuran; hexane / 2 h / -78 °C

17.2: 95 percent / tetrahydrofuran; hexane / 4 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; Li(O-Hex)2; 2,2,6,6-tetramethylpiperidinyl-lithium; 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; hexane; dichloromethane; water; acetone; toluene; benzene; 11.1: Peterson olefination;
DOI:10.1021/ol062960h