(2R,4aR,6S,8aR)-6-Methoxy-7,7-dimethyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

Base Information

Chemical Name:(2R,4aR,6S,8aR)-6-Methoxy-7,7-dimethyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one
CAS No.:121467-56-9
Molecular Formula:C₁₆H₂₀O₅
Molecular Weight:292.332
Hs Code.:

Synonyms:(2R,4aR,6S,8aR)-6-Methoxy-7,7-dimethyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

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Chemical Property of (2R,4aR,6S,8aR)-6-Methoxy-7,7-dimethyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

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Technology Process of (2R,4aR,6S,8aR)-6-Methoxy-7,7-dimethyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

There total 1 articles about (2R,4aR,6S,8aR)-6-Methoxy-7,7-dimethyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-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: 62.0%

: 63598-31-2
methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose

: 74-88-4
methyl iodide

: 121467-56-9
(2R,4aR,6S,8aR)-6-Methoxy-7,7-dimethyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

Guidance literature:: methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose; With potassium hydride; In tetrahydrofuran; at -78 ℃; for 2h;

methyl iodide; In tetrahydrofuran; at -78 - -20 ℃; for 1.66667h;
DOI:10.1021/ol061626i

Reference yield:

: 121467-56-9
(2R,4aR,6S,8aR)-6-Methoxy-7,7-dimethyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

: 913722-19-7
(2S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-one

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / H₂ / Pd(OH)2/C / methanol / 24 h / 20 °C / 760 Torr

2: 91 percent / imidazole / dimethylformamide / 2 h / 20 °C

3: 83 percent / acetonitrile / 22 h / 20 °C

4: 95 percent / Bu₃SnH; AIBN / toluene / 0.83 h / 90 °C

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; palladium dihydroxide; In methanol; N,N-dimethyl-formamide; toluene; acetonitrile; 4: Barton deoxygenation;
DOI:10.1021/ol061626i

Reference yield:

: 121467-56-9
(2R,4aR,6S,8aR)-6-Methoxy-7,7-dimethyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

: 913722-20-0
(2S,4S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / H₂ / Pd(OH)2/C / methanol / 24 h / 20 °C / 760 Torr

2: 91 percent / imidazole / dimethylformamide / 2 h / 20 °C

3: 83 percent / acetonitrile / 22 h / 20 °C

4: 95 percent / Bu₃SnH; AIBN / toluene / 0.83 h / 90 °C

5: 84 percent / Me₃Al; i-PrOH / hexane / 24 h / 20 °C

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); hydrogen; trimethylaluminum; tri-n-butyl-tin hydride; isopropyl alcohol; palladium dihydroxide; In methanol; hexane; N,N-dimethyl-formamide; toluene; acetonitrile; 4: Barton deoxygenation / 5: Meerwein-Ponndorf-Verley reduction;
DOI:10.1021/ol061626i