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

Base Information

Chemical Name:Toluene-4-sulfonic acid (3S,3aS,5aR,6R,9bS)-3,5a,9-trimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester
CAS No.:99297-03-7
Molecular Formula:C₂₂H₂₈O₅S
Molecular Weight:404.527
Hs Code.:

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

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

There total 16 articles about Toluene-4-sulfonic acid (3S,3aS,5aR,6R,9bS)-3,5a,9-trimethyl-2-oxo-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: 94.0%

: 76627-95-7,95782-13-1
Toluene-4-sulfonic acid (3S,3aS,5aR,6R,9S,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-2-oxo-dodecahydro-naphtho[1,2-b]furan-6-yl ester

: 95682-60-3,99297-03-7
Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester

Guidance literature:: With pyridine; thionyl chloride; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1016/S0040-4020(01)98812-X

Reference yield: 90.0%

: 41410-55-3
1-β-hydroxy-6β,7α,11β-H-eudesm-4-en-6,12-olide

: 98-59-9
p-toluenesulfonyl chloride

: 99297-03-7
Toluene-4-sulfonic acid (3S,3aS,5aR,6R,9bS)-3,5a,9-trimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydro-naphtho[1,2-b]furan-6-yl ester

Guidance literature:: With pyridine; for 20h; Ambient temperature;
DOI:10.1021/jo00350a081

Reference yield:

: 2-((1R,6R,7S,8S)-7-Hydroxy-1-methyl-2,5-bis-trimethylsilanyloxy-tricyclo[4.4.0.0^2,5]dec-8-yl)-propionic acid methyl ester

: 95682-60-3,99297-03-7
Toluene-4-sulfonic acid (3R,3aR,5aS,6S,9bR)-3,5a,9-trimethyl-2-oxo-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 9 steps

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

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

3: 80 percent / LiEt₃BH / tetrahydrofuran / 0.25 h / Ambient temperature

4: 96 percent / TsOH / 24 h / Ambient temperature

5: 93 percent / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

6: 97 percent / Amberlite IR 120 / methanol / 24 h / Ambient temperature

7: O₂ / Pt / H₂O / 24 h / 50 °C

8: 82 percent / pyridine / 120 h / Ambient temperature

9: 94 percent / pyridine, SOCl₂ / tetrahydrofuran / 1 h / 0 °C

With pyridine; hydrogenchloride; sodium periodate; thionyl chloride; Amberlite IR 120; oxygen; lithium triethylborohydride; toluene-4-sulfonic acid; triethylamine; platinum; In tetrahydrofuran; pyridine; methanol; diethyl ether; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)98812-X