(+)-octahydro-3,6α-dimethyl-3,12-epoxy-9β-(phenylthio)-12H-pyrano[4,3j]-1,2-benzodioxepin-10(3H)-one

Base Information

Chemical Name:(+)-octahydro-3,6α-dimethyl-3,12-epoxy-9β-(phenylthio)-12H-pyrano[4,3j]-1,2-benzodioxepin-10(3H)-one
CAS No.:467223-78-5
Molecular Formula:C₂₁H₂₆O₅S
Molecular Weight:390.5
Hs Code.:

Synonyms:(+)-octahydro-3,6α-dimethyl-3,12-epoxy-9β-(phenylthio)-12H-pyrano[4,3j]-1,2-benzodioxepin-10(3H)-one

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Chemical Property of (+)-octahydro-3,6α-dimethyl-3,12-epoxy-9β-(phenylthio)-12H-pyrano[4,3j]-1,2-benzodioxepin-10(3H)-one

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Technology Process of (+)-octahydro-3,6α-dimethyl-3,12-epoxy-9β-(phenylthio)-12H-pyrano[4,3j]-1,2-benzodioxepin-10(3H)-one

There total 1 articles about (+)-octahydro-3,6α-dimethyl-3,12-epoxy-9β-(phenylthio)-12H-pyrano[4,3j]-1,2-benzodioxepin-10(3H)-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: 67.0%

: 1212-08-4
S-Phenyl benzenethiosulfonate

: 63968-64-9
C₁₂H₁₃O₂(CH₃)3(O)(OO)

: 467223-78-5
(+)-octahydro-3,6α-dimethyl-3,12-epoxy-9β-(phenylthio)-12H-pyrano[4,3j]-1,2-benzodioxepin-10(3H)-one

Guidance literature:: C₁₂H₁₃O₂(CH₃)3(O)(OO); With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

S-Phenyl benzenethiosulfonate; In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1021/jm020142z

Reference yield:

: 467223-78-5
(+)-octahydro-3,6α-dimethyl-3,12-epoxy-9β-(phenylthio)-12H-pyrano[4,3j]-1,2-benzodioxepin-10(3H)-one

: (+)-octahydro-3,6α-dimethyl-3,12-epoxy-9β-(3'-(p-methanesulfonylphenyl)propyl)-12H-pyrano[4,3j]-1,2-benzoxepin-10(3H)-one

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / -78 °C

2: 38 percent / AIBN; tributyltin hydride / benzene / 9 h / Heating

3: DBU / tetrahydrofuran / 12 h

4: 94 percent / m-CPBA / CH₂Cl₂ / 4 h / -78 °C

5: 32 percent / H₂ / Pd/C / ethyl acetate / 7 h

With 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; benzene; 2: radical-induced Michael addition;
DOI:10.1021/jm030181q

Reference yield:

: 467223-78-5
(+)-octahydro-3,6α-dimethyl-3,12-epoxy-9β-(phenylthio)-12H-pyrano[4,3j]-1,2-benzodioxepin-10(3H)-one

: (+)-octahydro-3,6α-dimethyl-3,12-epoxy-9β-(3'-(3,5-bis-trifluoromethylphenyl)propyl)-12H-pyrano[4,3j]-1,2-benzoxepin-10(3H)-one

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / -78 °C

2: 43 percent / AIBN; tributyltin hydride / benzene / 9 h / Heating

3: DBU / tetrahydrofuran / 12 h / Heating

4: 21 percent / H₂ / Pd/C / ethyl acetate / 7 h

With 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; benzene; 2: radical-induced Michael addition;
DOI:10.1021/jm030181q