Trifluoro-methanesulfonic acid (3aR,4R,9R,9aR)-9-hydroxy-3-oxo-7-trifluoromethanesulfonyloxy-4-(3,4,5-trimethoxy-phenyl)-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-c]furan-6-yl ester

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Chemical Name:Trifluoro-methanesulfonic acid (3aR,4R,9R,9aR)-9-hydroxy-3-oxo-7-trifluoromethanesulfonyloxy-4-(3,4,5-trimethoxy-phenyl)-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-c]furan-6-yl ester
CAS No.:184873-28-7
Molecular Formula:C₂₃H₂₀F₆O₁₂S₂
Molecular Weight:666.527
Hs Code.:

Trifluoro-methanesulfonic acid (3aR,4R,9R,9aR)-9-hydroxy-3-oxo-7-trifluoromethanesulfonyloxy-4-(3,4,5-trimethoxy-phenyl)-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-c]furan-6-yl ester

Synonyms:Trifluoro-methanesulfonic acid (3aR,4R,9R,9aR)-9-hydroxy-3-oxo-7-trifluoromethanesulfonyloxy-4-(3,4,5-trimethoxy-phenyl)-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-c]furan-6-yl ester

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Chemical Property of Trifluoro-methanesulfonic acid (3aR,4R,9R,9aR)-9-hydroxy-3-oxo-7-trifluoromethanesulfonyloxy-4-(3,4,5-trimethoxy-phenyl)-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-c]furan-6-yl ester

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Technology Process of Trifluoro-methanesulfonic acid (3aR,4R,9R,9aR)-9-hydroxy-3-oxo-7-trifluoromethanesulfonyloxy-4-(3,4,5-trimethoxy-phenyl)-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-c]furan-6-yl ester

There total 2 articles about Trifluoro-methanesulfonic acid (3aR,4R,9R,9aR)-9-hydroxy-3-oxo-7-trifluoromethanesulfonyloxy-4-(3,4,5-trimethoxy-phenyl)-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-c]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: 68.0%

: 1174-97-6
6,7-O,O-demethylenepodophyllotoxin

: 358-23-6
trifluoromethylsulfonic anhydride

: 184873-28-7
Trifluoro-methanesulfonic acid (3aR,4R,9R,9aR)-9-hydroxy-3-oxo-7-trifluoromethanesulfonyloxy-4-(3,4,5-trimethoxy-phenyl)-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-c]furan-6-yl ester

Guidance literature:: With 2,6-dimethylpyridine; dmap; In dichloromethane; at 0 ℃;
DOI:10.1016/0040-4020(96)00862-9

Reference yield:

: 518-28-5
podofilox

: 184873-28-7
Trifluoro-methanesulfonic acid (3aR,4R,9R,9aR)-9-hydroxy-3-oxo-7-trifluoromethanesulfonyloxy-4-(3,4,5-trimethoxy-phenyl)-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-c]furan-6-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) BCl₃, 2.) aq. BaCO₃ / 1.) CH₂Cl₂, -78 deg C, 3 h, 2.) acetone, reflux, 3 h

2: 68 percent / 2,6-lutidine, DMAP / CH₂Cl₂ / 0 °C

With 2,6-dimethylpyridine; dmap; boron trichloride; barium carbonate; In dichloromethane;
DOI:10.1016/0040-4020(96)00862-9

Reference yield:

: 184873-28-7
Trifluoro-methanesulfonic acid (3aR,4R,9R,9aR)-9-hydroxy-3-oxo-7-trifluoromethanesulfonyloxy-4-(3,4,5-trimethoxy-phenyl)-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-c]furan-6-yl ester

: 184873-33-4
(3aR,4R,9R,9aR)-4-(tert-Butyl-dimethyl-silanyloxy)-1-oxo-9-(3,4,5-trimethoxy-phenyl)-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-c]furan-6,7-dicarbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1: 50 percent / LiCl, Pd(PPh₃)4 / dioxane / 95 °C

2: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

3: 21 percent / LDA / tetrahydrofuran / 0.25 h / -78 °C

4: 90 percent / OsO₄, N-methylmorpholine-N-oxide / acetone; H₂O; 2-methyl-propan-2-ol / 5.5 h / 0 °C

5: 91 percent / Pb(OAc)4 / benzene; CH₂Cl₂ / 5 h / Ambient temperature

With 2,6-dimethylpyridine; lead(IV) acetate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 4-methylmorpholine N-oxide; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetone; tert-butyl alcohol; benzene;
DOI:10.1016/0040-4020(96)00862-9