(1R,3aR,4R,4aR,8aS,9aR)-dodecahydro-1-methoxy-4-(phenylthio)methylnaphtho[2,3-c]furan

Base Information

Chemical Name:(1R,3aR,4R,4aR,8aS,9aR)-dodecahydro-1-methoxy-4-(phenylthio)methylnaphtho[2,3-c]furan
CAS No.:479195-76-1
Molecular Formula:C₂₀H₂₈O₂S
Molecular Weight:332.507
Hs Code.:

Synonyms:(1R,3aR,4R,4aR,8aS,9aR)-dodecahydro-1-methoxy-4-(phenylthio)methylnaphtho[2,3-c]furan

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Chemical Property of (1R,3aR,4R,4aR,8aS,9aR)-dodecahydro-1-methoxy-4-(phenylthio)methylnaphtho[2,3-c]furan

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Technology Process of (1R,3aR,4R,4aR,8aS,9aR)-dodecahydro-1-methoxy-4-(phenylthio)methylnaphtho[2,3-c]furan

There total 13 articles about (1R,3aR,4R,4aR,8aS,9aR)-dodecahydro-1-methoxy-4-(phenylthio)methylnaphtho[2,3-c]furan 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: 76.0%

: 108-98-5
thiophenol

: 479195-75-0
(1R,3aS,4R,4aR,8aS,9aR)-dodecahydro-1-methoxynaphtho[2,3-c]furan-4-methanol

: 479195-76-1
(1R,3aR,4R,4aR,8aS,9aR)-dodecahydro-1-methoxy-4-(phenylthio)methylnaphtho[2,3-c]furan

Guidance literature:: With N-ethyl-N,N-diisopropylamine; (cyanomethyl)trimethyl-phosphonium iodide; In acetonitrile; at 80 ℃; for 2.5h;
DOI:10.1016/S0960-894X(02)00695-9

Reference yield:

: 91632-72-3
4,5,6,7-tetrahydroisobenzofuran

: 479195-76-1
(1R,3aR,4R,4aR,8aS,9aR)-dodecahydro-1-methoxy-4-(phenylthio)methylnaphtho[2,3-c]furan

Guidance literature:: Multi-step reaction with 13 steps

1.1: 49 percent / LiClO₄; 4,4'-thiobis(6-tert-butyl-m-cresol) / diethyl ether / 48 h / 20 °C

2.1: 98 percent / H₂ / 10 percent Pd/C / ethanol / 5 h / 20 °C / 760 Torr

3.1: 99 percent / LiN(TMS)2 / tetrahydrofuran / -70 - -40 °C

4.1: 70 percent / DBU / toluene / 4 h / 80 °C

5.1: 95 percent / H₂ / PtO₂ / ethanol / 2 h / 20 °C / 760 Torr

6.1: 85 percent / DIBAL-H / diethyl ether; hexane / 1 h / -70 °C

7.1: 4.56 g / BF₃*OEt₂ / CH₂Cl₂ / -70 - 20 °C

8.1: 97 percent / 4-methylmorpholine N-oxide; molecular sieves 4 Angstroem; TPAP / CH₂Cl₂ / 1 h / 20 °C

9.1: NaN(TMS)2 / diethyl ether; toluene / 0.5 h / 20 °C

9.2: 54 percent / dimethylsulfoxide; toluene / -78 - 20 °C

10.1: BH₃*THF / tetrahydrofuran / 7 h / 20 °C

10.2: 82 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

11.1: 32 percent / Et₃N / CH₂Cl₂ / 18 h / 0 - 20 °C

12.1: 91 percent / aq. NaOH / ethanol / 20 °C

13.1: 76 percent / (cyanomethyl)trimethylphosphonium iodide; iPr₂NEt / acetonitrile / 80 °C

With sodium hydroxide; Santonox R; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; lithium perchlorate; sodium hexamethyldisilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; (cyanomethyl)trimethyl-phosphonium iodide; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; toluene; acetonitrile; 1.1: Diels-Alder reaction / 9.2: Wittig reaction;
DOI:10.1016/S0968-0896(02)00665-X

Reference yield:

: (+/-)-(3aR,4S,9R,9aR)-4,9-epoxy-3a,4,5,6,7,8,9,9a-octahydronaphtho[2,3-c]furan-1(3H)-one

: 479195-76-1
(1R,3aR,4R,4aR,8aS,9aR)-dodecahydro-1-methoxy-4-(phenylthio)methylnaphtho[2,3-c]furan

Guidance literature:: Multi-step reaction with 12 steps

1.1: 98 percent / H₂ / 10 percent Pd/C / ethanol / 5 h / 20 °C / 760 Torr

2.1: 99 percent / LiN(TMS)2 / tetrahydrofuran / -70 - -40 °C

3.1: 70 percent / DBU / toluene / 4 h / 80 °C

4.1: 95 percent / H₂ / PtO₂ / ethanol / 2 h / 20 °C / 760 Torr

5.1: 85 percent / DIBAL-H / diethyl ether; hexane / 1 h / -70 °C

6.1: 4.56 g / BF₃*OEt₂ / CH₂Cl₂ / -70 - 20 °C

7.1: 97 percent / 4-methylmorpholine N-oxide; molecular sieves 4 Angstroem; TPAP / CH₂Cl₂ / 1 h / 20 °C

8.1: NaN(TMS)2 / diethyl ether; toluene / 0.5 h / 20 °C

8.2: 54 percent / dimethylsulfoxide; toluene / -78 - 20 °C

9.1: BH₃*THF / tetrahydrofuran / 7 h / 20 °C

9.2: 82 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

10.1: 32 percent / Et₃N / CH₂Cl₂ / 18 h / 0 - 20 °C

11.1: 91 percent / aq. NaOH / ethanol / 20 °C

12.1: 76 percent / (cyanomethyl)trimethylphosphonium iodide; iPr₂NEt / acetonitrile / 80 °C

With sodium hydroxide; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; sodium hexamethyldisilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; (cyanomethyl)trimethyl-phosphonium iodide; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; toluene; acetonitrile; 8.2: Wittig reaction;
DOI:10.1016/S0968-0896(02)00665-X