(3R,4S,5S)-3-Cyclohex-1-enyl-3,4-dimethyl-5-trityloxymethyl-dihydro-furan-2-one

Base Information

Chemical Name:(3R,4S,5S)-3-Cyclohex-1-enyl-3,4-dimethyl-5-trityloxymethyl-dihydro-furan-2-one
CAS No.:892867-38-8
Molecular Formula:C₃₂H₃₄O₃
Molecular Weight:466.62
Hs Code.:

Synonyms:(3R,4S,5S)-3-Cyclohex-1-enyl-3,4-dimethyl-5-trityloxymethyl-dihydro-furan-2-one

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Chemical Property of (3R,4S,5S)-3-Cyclohex-1-enyl-3,4-dimethyl-5-trityloxymethyl-dihydro-furan-2-one

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Technology Process of (3R,4S,5S)-3-Cyclohex-1-enyl-3,4-dimethyl-5-trityloxymethyl-dihydro-furan-2-one

There total 1 articles about (3R,4S,5S)-3-Cyclohex-1-enyl-3,4-dimethyl-5-trityloxymethyl-dihydro-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: 91.0%

: (3S,4S,5S)-3,4-Dimethyl-5-trityloxymethyl-dihydro-furan-2-one

: 108-94-1,11119-77-0,9003-41-2,9075-99-4
cyclohexanone

: 892867-38-8
(3R,4S,5S)-3-Cyclohex-1-enyl-3,4-dimethyl-5-trityloxymethyl-dihydro-furan-2-one

Guidance literature:: (3S,4S,5S)-3,4-Dimethyl-5-trityloxymethyl-dihydro-furan-2-one; cyclohexanone; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.166667h;

With pyridine; thionyl chloride; at 0 ℃; for 1h;
DOI:10.1016/j.tetlet.2006.03.078

Reference yield:

: 892867-38-8
(3R,4S,5S)-3-Cyclohex-1-enyl-3,4-dimethyl-5-trityloxymethyl-dihydro-furan-2-one

: 892867-39-9
(2R,3S,4S)-2-Cyclohex-1-enyl-2,3-dimethyl-5-trityloxy-pentane-1,4-diol

Guidance literature:: With lithium borohydride; In tetrahydrofuran; at 65 ℃; for 38h;
DOI:10.1016/j.tetlet.2006.03.078

Reference yield:

: 892867-38-8
(3R,4S,5S)-3-Cyclohex-1-enyl-3,4-dimethyl-5-trityloxymethyl-dihydro-furan-2-one

: 892867-46-8
(3aR,4S,5S,6R,6aS,10aS)-6-Benzyloxymethyl-2,2,5,6-tetramethyl-octahydro-naphtho[1,8a-d][1,3]dioxol-4-ol

Guidance literature:: Multi-step reaction with 10 steps

1: LiBH₄ / tetrahydrofuran / 38 h / 65 °C

2: K₂CO₃; 18-crown-6-ether / acetonitrile / 8 h / 50 °C

3: DBU / acetonitrile / 20 h / 65 °C

4: 86 percent / SeO₂ / dioxane; H₂O / 17 h / 90 °C

5: 77 percent / NaBH₄; NiCl₂*6H₂O / methanol; CH₂Cl₂ / 0.17 h / 0 °C

6: Et₂AlCl / CH₂Cl₂ / 0.5 h / -78 - 0 °C

7: PCC; Al₂O₃ / CH₂Cl₂ / 6 h / 20 °C

8: SmI₂; t-BuOH / tetrahydrofuran / 0.5 h / -78 °C

9: PPTS / CH₂Cl₂ / 8 h / 20 °C

10: TBAF / tetrahydrofuran / 15 h / 50 °C

With aluminum oxide; sodium tetrahydroborate; lithium borohydride; selenium(IV) oxide; samarium diiodide; 18-crown-6 ether; tetrabutyl ammonium fluoride; diethylaluminium chloride; pyridinium p-toluenesulfonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; nickel dichloride; tert-butyl alcohol; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetonitrile;
DOI:10.1016/j.tetlet.2006.03.078