Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2,8-dioxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester

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Chemical Name:Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2,8-dioxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester
CAS No.:95682-61-4
Molecular Formula:C₂₂H₂₆O₆S
Molecular Weight:418.511
Hs Code.:

Synonyms:

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Chemical Property of Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2,8-dioxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester

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Technology Process of Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2,8-dioxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester

There total 14 articles about Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2,8-dioxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester 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:

: 1193-18-6
3-methylcyclohexen-2-one

: 95682-61-4
Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2,8-dioxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 1) LDA, HMPA / 1) THF, -78 deg C: 2) -20 deg C, 2 h

2: hexane / 504 h / Irradiation

3: NaBH₄ / methanol / 1 h / -20 °C

4: 1) HCl, 2) NaIO₄ aq / 1) MeOH, 1 h, RT; 2) H₂O-MeOH, 30 min, 25 deg C

5: 98 percent / triethylamine / dimethylformamide / 2 h / Ambient temperature

6: 80 percent / LiEt₃BH / tetrahydrofuran / 0.25 h / Ambient temperature

7: 96 percent / TsOH / 24 h / Ambient temperature

8: 93 percent / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

9: 97 percent / Amberlite IR 120 / methanol / 24 h / Ambient temperature

10: O₂ / Pt / H₂O / 24 h / 50 °C

11: 82 percent / pyridine / 120 h / Ambient temperature

12: 94 percent / pyridine, SOCl₂ / tetrahydrofuran / 1 h / 0 °C

13: 1) NBS, AIBN 2) (Bu₄N)2Cr₂O₇ / 1) CCl₄, 20 min, reflux; 2) CHCl₃, 2 h, reflux

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; thionyl chloride; 2,2'-azobis(isobutyronitrile); (Bu₄N)2Cr₂O₇; Amberlite IR 120; oxygen; lithium triethylborohydride; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; platinum; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)98812-X

Reference yield:

: 95682-51-2,118139-09-6,118139-10-9,132620-74-7,132620-75-8,143729-72-0,143729-73-1
2S-(1,2,3,4,4a,5,6,7,8,8aα-decahydro-1α,5β,8β-trihydroxy-4aβ,8α-dimethyl-naphtalen-2β-yl)-propanol

: 95682-61-4
Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2,8-dioxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: O₂ / Pt / H₂O / 24 h / 50 °C

2: 82 percent / pyridine / 120 h / Ambient temperature

3: 94 percent / pyridine, SOCl₂ / tetrahydrofuran / 1 h / 0 °C

4: 1) NBS, AIBN 2) (Bu₄N)2Cr₂O₇ / 1) CCl₄, 20 min, reflux; 2) CHCl₃, 2 h, reflux

With pyridine; N-Bromosuccinimide; thionyl chloride; 2,2'-azobis(isobutyronitrile); (Bu₄N)2Cr₂O₇; oxygen; platinum; In tetrahydrofuran; pyridine; water;
DOI:10.1016/S0040-4020(01)98812-X

Reference yield:

: 95682-52-3
2S-(1,2,3,4,4a,5,6,7,8,8aα-decahydro-5β-hydroxy-4aβ-methyl-1α-trimethylsilyloxy-8-oxo-naphtalen-2β-yl)-propanol

: 95682-61-4
Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2,8-dioxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / TsOH / 24 h / Ambient temperature

2: 93 percent / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

3: 97 percent / Amberlite IR 120 / methanol / 24 h / Ambient temperature

4: O₂ / Pt / H₂O / 24 h / 50 °C

5: 82 percent / pyridine / 120 h / Ambient temperature

6: 94 percent / pyridine, SOCl₂ / tetrahydrofuran / 1 h / 0 °C

7: 1) NBS, AIBN 2) (Bu₄N)2Cr₂O₇ / 1) CCl₄, 20 min, reflux; 2) CHCl₃, 2 h, reflux

With pyridine; N-Bromosuccinimide; thionyl chloride; 2,2'-azobis(isobutyronitrile); (Bu₄N)2Cr₂O₇; Amberlite IR 120; oxygen; toluene-4-sulfonic acid; platinum; In tetrahydrofuran; pyridine; methanol; diethyl ether; water;
DOI:10.1016/S0040-4020(01)98812-X