((1S,3R,3aR,4R,4aS,7aR)-4-(benzyloxymethyl)-3-methyl-3,3a,4,4a,5,6,7,7a-octahydro-1H-indeno[5,6-c]furan-1,3-diyl)dimethanol

Base Information

Chemical Name:((1S,3R,3aR,4R,4aS,7aR)-4-(benzyloxymethyl)-3-methyl-3,3a,4,4a,5,6,7,7a-octahydro-1H-indeno[5,6-c]furan-1,3-diyl)dimethanol
CAS No.:1313493-20-7
Molecular Formula:C₂₂H₃₀O₄
Molecular Weight:358.478
Hs Code.:

Synonyms:((1S,3R,3aR,4R,4aS,7aR)-4-(benzyloxymethyl)-3-methyl-3,3a,4,4a,5,6,7,7a-octahydro-1H-indeno[5,6-c]furan-1,3-diyl)dimethanol

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Chemical Property of ((1S,3R,3aR,4R,4aS,7aR)-4-(benzyloxymethyl)-3-methyl-3,3a,4,4a,5,6,7,7a-octahydro-1H-indeno[5,6-c]furan-1,3-diyl)dimethanol

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Technology Process of ((1S,3R,3aR,4R,4aS,7aR)-4-(benzyloxymethyl)-3-methyl-3,3a,4,4a,5,6,7,7a-octahydro-1H-indeno[5,6-c]furan-1,3-diyl)dimethanol

There total 14 articles about ((1S,3R,3aR,4R,4aS,7aR)-4-(benzyloxymethyl)-3-methyl-3,3a,4,4a,5,6,7,7a-octahydro-1H-indeno[5,6-c]furan-1,3-diyl)dimethanol 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%

: 1313493-19-4
C₃₄H₅₈O₄Si₂

: 1313493-20-7
((1S,3R,3aR,4R,4aS,7aR)-4-(benzyloxymethyl)-3-methyl-3,3a,4,4a,5,6,7,7a-octahydro-1H-indeno[5,6-c]furan-1,3-diyl)dimethanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1.25h;
DOI:10.1021/jo200899v

Reference yield:

: 1313493-11-6
(2R)-3-(4-methoxybenzyloxy)-5-methylhex-5-ene-1,2-diol

: 1313493-20-7
((1S,3R,3aR,4R,4aS,7aR)-4-(benzyloxymethyl)-3-methyl-3,3a,4,4a,5,6,7,7a-octahydro-1H-indeno[5,6-c]furan-1,3-diyl)dimethanol

Guidance literature:: Multi-step reaction with 12 steps

1.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 16 h / 20 °C

2.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 20 °C / pH 7 / aq. buffer

4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

5.2: 1 h / -78 - 20 °C

6.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

7.1: quinoline; hydrogen / ethyl acetate / 4 h

8.1: manganese(IV) oxide / dichloromethane / 36 h / 20 °C

9.1: 2,6-di-tert-butyl-4-methyl-phenol / toluene / 15 h / 140 °C

10.1: sodium tetrahydroborate / ethanol / 1 h / 0 - 20 °C

11.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / 0 - 20 °C

11.2: 3 h / 0 - 20 °C

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.25 h / 20 °C

With quinoline; dmap; manganese(IV) oxide; sodium tetrahydroborate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrapropylammonium perruthennate; 2,6-di-tert-butyl-4-methyl-phenol; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 6.1: Sonogashira coupling / 9.1: Diels-Alder reaction;
DOI:10.1021/jo200899v

Reference yield:

: 1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-but-3-en-1-ol

: 1313493-20-7
((1S,3R,3aR,4R,4aS,7aR)-4-(benzyloxymethyl)-3-methyl-3,3a,4,4a,5,6,7,7a-octahydro-1H-indeno[5,6-c]furan-1,3-diyl)dimethanol

Guidance literature:: Multi-step reaction with 14 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C

1.2: 2 h / 0 - 20 °C

2.1: water; acetic acid / tetrahydrofuran / 15 h / 40 °C

3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 16 h / 20 °C

4.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 20 °C / pH 7 / aq. buffer

6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C

7.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

7.2: 1 h / -78 - 20 °C

8.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

9.1: quinoline; hydrogen / ethyl acetate / 4 h

10.1: manganese(IV) oxide / dichloromethane / 36 h / 20 °C

11.1: 2,6-di-tert-butyl-4-methyl-phenol / toluene / 15 h / 140 °C

12.1: sodium tetrahydroborate / ethanol / 1 h / 0 - 20 °C

13.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / 0 - 20 °C

13.2: 3 h / 0 - 20 °C

14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.25 h / 20 °C

With quinoline; dmap; manganese(IV) oxide; sodium tetrahydroborate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrapropylammonium perruthennate; 2,6-di-tert-butyl-4-methyl-phenol; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 8.1: Sonogashira coupling / 11.1: Diels-Alder reaction;
DOI:10.1021/jo200899v