(1S,3S,3aS,4R,4aS,8aR,9aS)-dodecahydro-1-methoxy-3-methyl-4-[(phenylsulfonyl)methyl]naphtho[2,3-c]furan

Base Information

Chemical Name:(1S,3S,3aS,4R,4aS,8aR,9aS)-dodecahydro-1-methoxy-3-methyl-4-[(phenylsulfonyl)methyl]naphtho[2,3-c]furan
CAS No.:192133-39-4
Molecular Formula:C₂₁H₃₀O₄S
Molecular Weight:378.533
Hs Code.:

Synonyms:(1S,3S,3aS,4R,4aS,8aR,9aS)-dodecahydro-1-methoxy-3-methyl-4-[(phenylsulfonyl)methyl]naphtho[2,3-c]furan

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Chemical Property of (1S,3S,3aS,4R,4aS,8aR,9aS)-dodecahydro-1-methoxy-3-methyl-4-[(phenylsulfonyl)methyl]naphtho[2,3-c]furan

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Technology Process of (1S,3S,3aS,4R,4aS,8aR,9aS)-dodecahydro-1-methoxy-3-methyl-4-[(phenylsulfonyl)methyl]naphtho[2,3-c]furan

There total 25 articles about (1S,3S,3aS,4R,4aS,8aR,9aS)-dodecahydro-1-methoxy-3-methyl-4-[(phenylsulfonyl)methyl]naphtho[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: 94.0%

: 192133-37-2
(1S,3S,3aS,4R,4aS,8aR,9aS)-1-Methoxy-3-methyl-4-phenylsulfanylmethyl-dodecahydro-naphtho[2,3-c]furan

: 192133-39-4
(1S,3S,3aS,4R,4aS,8aR,9aS)-dodecahydro-1-methoxy-3-methyl-4-[(phenylsulfonyl)methyl]naphtho[2,3-c]furan

Guidance literature:: With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 2h; Ambient temperature;
DOI:10.1021/jo970612a

Reference yield:

: 92694-51-4
(S)-(+)-β-angelica lactone

: 192133-39-4
(1S,3S,3aS,4R,4aS,8aR,9aS)-dodecahydro-1-methoxy-3-methyl-4-[(phenylsulfonyl)methyl]naphtho[2,3-c]furan

Guidance literature:: Multi-step reaction with 13 steps

1.1: lithium perchlorate / diethyl ether / 168 h / 20 °C

2.1: 96 percent / H₂ / 10 percent Pd/C / ethanol / 12 h / 20 °C / 760 Torr

3.1: 92 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C

4.1: 83 percent / DBU / toluene / 5 h / 100 °C

5.1: 96 percent / H₂ / PtO₂ / ethanol / 16 h / 20 °C / 760 Torr

6.1: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C

7.1: 1.50 g / BF₃*Et₂O / CH₂Cl₂ / 12 h / -60 °C

8.1: 95 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / 20 °C

9.1: NaN(TMS)2 / diethyl ether; toluene / 1 h / 20 °C

9.2: 86 percent / diethyl ether; toluene / 2 h / 20 °C

10.1: BH₃*THF / tetrahydrofuran / 3 h / -78 °C

10.2: 73 percent / aq. NaOH; H₂O₂ / 0.5 h / 0 °C

11.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 0 °C

12.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C

13.1: 82 percent / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH₂Cl₂ / 2 h / 20 °C

With dmap; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; lithium perchlorate; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; toluene; 1.1: Diels-Alder reaction / 9.2: Wittig reaction;
DOI:10.1016/S0040-4020(02)01358-3

Reference yield:

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

: 192133-39-4
(1S,3S,3aS,4R,4aS,8aR,9aS)-dodecahydro-1-methoxy-3-methyl-4-[(phenylsulfonyl)methyl]naphtho[2,3-c]furan

Guidance literature:: Multi-step reaction with 13 steps

1.1: lithium perchlorate / diethyl ether / 168 h / 20 °C

2.1: 96 percent / H₂ / 10 percent Pd/C / ethanol / 12 h / 20 °C / 760 Torr

3.1: 92 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C

4.1: 83 percent / DBU / toluene / 5 h / 100 °C

5.1: 96 percent / H₂ / PtO₂ / ethanol / 16 h / 20 °C / 760 Torr

6.1: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C

7.1: 1.50 g / BF₃*Et₂O / CH₂Cl₂ / 12 h / -60 °C

8.1: 95 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / 20 °C

9.1: NaN(TMS)2 / diethyl ether; toluene / 1 h / 20 °C

9.2: 86 percent / diethyl ether; toluene / 2 h / 20 °C

10.1: BH₃*THF / tetrahydrofuran / 3 h / -78 °C

10.2: 73 percent / aq. NaOH; H₂O₂ / 0.5 h / 0 °C

11.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 0 °C

12.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C

13.1: 82 percent / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH₂Cl₂ / 2 h / 20 °C

With dmap; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; lithium perchlorate; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; toluene; 1.1: Diels-Alder reaction / 9.2: Wittig reaction;
DOI:10.1016/S0040-4020(02)01358-3