(5R,6R,7aR,8S,9R)-8-vinyl-6,7-dihydro-9-(benzyloxy)-6-methyl-5H-5,7a-ethano-2H-furo[3,2-b]pyran-2-one

Base Information

Chemical Name:(5R,6R,7aR,8S,9R)-8-vinyl-6,7-dihydro-9-(benzyloxy)-6-methyl-5H-5,7a-ethano-2H-furo[3,2-b]pyran-2-one
CAS No.:1392307-63-9
Molecular Formula:C₁₉H₂₀O₄
Molecular Weight:312.365
Hs Code.:

Synonyms:(5R,6R,7aR,8S,9R)-8-vinyl-6,7-dihydro-9-(benzyloxy)-6-methyl-5H-5,7a-ethano-2H-furo[3,2-b]pyran-2-one

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Chemical Property of (5R,6R,7aR,8S,9R)-8-vinyl-6,7-dihydro-9-(benzyloxy)-6-methyl-5H-5,7a-ethano-2H-furo[3,2-b]pyran-2-one

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Technology Process of (5R,6R,7aR,8S,9R)-8-vinyl-6,7-dihydro-9-(benzyloxy)-6-methyl-5H-5,7a-ethano-2H-furo[3,2-b]pyran-2-one

There total 20 articles about (5R,6R,7aR,8S,9R)-8-vinyl-6,7-dihydro-9-(benzyloxy)-6-methyl-5H-5,7a-ethano-2H-furo[3,2-b]pyran-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: 85.0%

: 1392307-79-7
(E)-ethyl 2-((1R,4R,5S,6R,7R)-6-(benzyloxy)-4-hydroxy-7-methyl-5-vinyl-2-oxabicyclo[2.2.2]octan-3-ylidene)acetate

: 1392307-63-9
(5R,6R,7aR,8S,9R)-8-vinyl-6,7-dihydro-9-(benzyloxy)-6-methyl-5H-5,7a-ethano-2H-furo[3,2-b]pyran-2-one

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1039/c3ob40692j

Reference yield:

: (S)-4-benzyl-3-((2S,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-enoyl)oxazolidin-2-one

: 1392307-63-9
(5R,6R,7aR,8S,9R)-8-vinyl-6,7-dihydro-9-(benzyloxy)-6-methyl-5H-5,7a-ethano-2H-furo[3,2-b]pyran-2-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: sodium tetrahydroborate / tetrahydrofuran; water / 0 - 20 °C

2.1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C

3.1: dichloromethane / 20 h

4.1: diisobutylaluminium hydride / diethyl ether; toluene / -40 °C / Inert atmosphere

5.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / Cooling with ice

6.2: 0.25 h

7.1: pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

8.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere

9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C

9.2: 2 h

10.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / hexane; toluene / 0.5 h / -78 °C

10.2: -78 - 0 °C

10.3: 9 h / 60 °C

11.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) / isopropyl alcohol / 2.5 h / 70 °C / Inert atmosphere

12.1: sodium isopropylate / isopropyl alcohol / 2 h / UV-irradiation

With pyrrolidine; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); carbon tetrabromide; sodium isopropylate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; isopropyl alcohol; toluene; 2.1: Dess-Martin oxidation / 3.1: Wittig reaction / 7.1: Tsuji-Trost cyclization;
DOI:10.1002/anie.201108223

Reference yield:

: 1392307-50-4
(2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol

: 1392307-63-9
(5R,6R,7aR,8S,9R)-8-vinyl-6,7-dihydro-9-(benzyloxy)-6-methyl-5H-5,7a-ethano-2H-furo[3,2-b]pyran-2-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C

2.1: dichloromethane / 20 h

3.1: diisobutylaluminium hydride / diethyl ether; toluene / -40 °C / Inert atmosphere

4.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / Cooling with ice

5.2: 0.25 h

6.1: pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

7.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere

8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C

8.2: 2 h

9.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / hexane; toluene / 0.5 h / -78 °C

9.2: -78 - 0 °C

9.3: 9 h / 60 °C

10.1: [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) / isopropyl alcohol / 2.5 h / 70 °C / Inert atmosphere

11.1: sodium isopropylate / isopropyl alcohol / 2 h / UV-irradiation

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); carbon tetrabromide; sodium isopropylate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; isopropyl alcohol; toluene; 1.1: Dess-Martin oxidation / 2.1: Wittig reaction / 6.1: Tsuji-Trost cyclization;
DOI:10.1002/anie.201108223