(3aR,4R,5R,6aS)-4-[(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2,5-diol

Base Information

Chemical Name:(3aR,4R,5R,6aS)-4-[(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2,5-diol
CAS No.:118888-96-3
Molecular Formula:C₃₁H₄₄O₄Si
Molecular Weight:508.773
Hs Code.:

Synonyms:(3aR,4R,5R,6aS)-4-[(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2,5-diol

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Chemical Property of (3aR,4R,5R,6aS)-4-[(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2,5-diol

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Technology Process of (3aR,4R,5R,6aS)-4-[(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2,5-diol

There total 10 articles about (3aR,4R,5R,6aS)-4-[(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2,5-diol 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: 77.0%

: 118888-95-2,119008-06-9
(3aR,4R,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-2-methoxy-hexahydro-cyclopenta[b]furan

: 118888-96-3
(3aR,4R,5R,6aS)-4-[(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2,5-diol

Guidance literature:: With hydrogenchloride; In acetonitrile; for 2h;
DOI:10.1016/S0040-4020(01)86203-7

Reference yield:

: 32233-40-2
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

: 118888-96-3
(3aR,4R,5R,6aS)-4-[(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2,5-diol

Guidance literature:: Multi-step reaction with 10 steps

1: pyridine / 48 h / -18 °C

2: 1) t-BuOK / 1) DMSO, RT, 2) DMSO, 30 min

3: DIBAL / toluene; CH₂Cl₂ / 0.5 h / -78 °C

4: BF₃*Et₂O / 2 h / -20 °C

5: imidazole / dimethylformamide / 0.17 h / 40 °C

6: 80percent m-chloroperbenzoic acid / CH₂Cl₂ / 1) -78 to 0 deg C, 30 min,2) 0 deg C,2 h

7: 1) n-butyllithium, 2) BF₃*Et₂O / 1) THF, hexane, -78 deg C, 5 min,2) THF, hexane, 10 min, 3) THF, hexane, -30 deg C, 2 h

8: pyridine / 15 h / Ambient temperature

9: 6percent sodium amalgam / tetrahydrofuran; methanol / 3 h / Ambient temperature

10: 77 percent / 0.3N hydrochloric acid / acetonitrile / 2 h

With pyridine; 1H-imidazole; hydrogenchloride; sodium amalgam; n-butyllithium; boron trifluoride diethyl etherate; potassium tert-butylate; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4020(01)86203-7

Reference yield:

: 118888-93-0
(S)-1-Benzenesulfonyl-1-[(3aR,4R,5R,6aS)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-3-(tert-butyl-diphenyl-silanyloxy)-octan-2-ol

: 118888-96-3
(3aR,4R,5R,6aS)-4-[(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2,5-diol

Guidance literature:: Multi-step reaction with 3 steps

1: pyridine / 15 h / Ambient temperature

2: 6percent sodium amalgam / tetrahydrofuran; methanol / 3 h / Ambient temperature

3: 77 percent / 0.3N hydrochloric acid / acetonitrile / 2 h

With pyridine; hydrogenchloride; sodium amalgam; In tetrahydrofuran; methanol; acetonitrile;
DOI:10.1016/S0040-4020(01)86203-7