2β-(2,6-dimethoxyphenoxy)-1α-hydroxy-6α-<2-methoxy-4-(3,4-methylenedioxybenzyloxy)phenyl>-3,7-dioxabicyclo<3.3.0>octane

Base Information

Chemical Name:2β-(2,6-dimethoxyphenoxy)-1α-hydroxy-6α-<2-methoxy-4-(3,4-methylenedioxybenzyloxy)phenyl>-3,7-dioxabicyclo<3.3.0>octane
CAS No.:142206-85-7
Molecular Formula:C₂₉H₃₀O₁₀
Molecular Weight:538.551
Hs Code.:

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Chemical Property of 2β-(2,6-dimethoxyphenoxy)-1α-hydroxy-6α-<2-methoxy-4-(3,4-methylenedioxybenzyloxy)phenyl>-3,7-dioxabicyclo<3.3.0>octane

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Technology Process of 2β-(2,6-dimethoxyphenoxy)-1α-hydroxy-6α-<2-methoxy-4-(3,4-methylenedioxybenzyloxy)phenyl>-3,7-dioxabicyclo<3.3.0>octane

There total 107 articles about 2β-(2,6-dimethoxyphenoxy)-1α-hydroxy-6α-<2-methoxy-4-(3,4-methylenedioxybenzyloxy)phenyl>-3,7-dioxabicyclo<3.3.0>octane 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: 74.0%

: [(1R,3aR,4S,6aS)-1-[4-(Benzo[1,3]dioxol-5-ylmethoxy)-2-methoxy-phenyl]-4-(2,6-dimethoxy-phenoxy)-dihydro-furo[3,4-c]furan-3a-yloxy]-tert-butyl-dimethyl-silane

: 142206-85-7,142236-89-3,142236-90-6,142236-91-7
2α-(2,6-dimethoxyphenoxy)-1α-hydroxy-6α-<2-methoxy-4-(3,4-methylenedioxybenzyloxy)phenyl>-3,7-dioxabicyclo<3.3.0>octane

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; acetonitrile; for 20h; Ambient temperature;

Reference yield: 70.0%

: [(1S,3aR,4S,6aS)-1-[4-(Benzo[1,3]dioxol-5-ylmethoxy)-2-methoxy-phenyl]-4-(2,6-dimethoxy-phenoxy)-dihydro-furo[3,4-c]furan-3a-yloxy]-tert-butyl-dimethyl-silane

: 142206-85-7,142236-89-3,142236-90-6,142236-91-7
2α-(2,6-dimethoxyphenoxy)-1α-hydroxy-6β-<2-methoxy-4-(3,4-methylenedioxybenzyloxy)phenyl>-3,7-dioxabicyclo<3.3.0>octane

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; acetonitrile; for 20h; Ambient temperature;

Reference yield:

: 95332-26-6
2-hydroxy-4-(methoxymethyloxy)benzaldehyde

: 142206-85-7,142236-89-3,142236-90-6,142236-91-7
2α-(2,6-dimethoxyphenoxy)-1α-hydroxy-6β-<2-methoxy-4-(3,4-methylenedioxybenzyloxy)phenyl>-3,7-dioxabicyclo<3.3.0>octane

Guidance literature:: Multi-step reaction with 18 steps

1: 86 percent / NaOH, Adogen 464 / H₂O; CH₂Cl₂ / 5 h / Ambient temperature

2: 1) LDA / 1) THF, hexane, -75 deg C, 30 min, 2) THF, hexane, -75 deg C, 3 h

3: 83 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / Ambient temperature

4: 90 percent / LiAlH₄ / diethyl ether / 0.5 h / -10 °C

5: 1) 2percent aq. OsO₄, N-methylmorpholine N-oxide, 2) NaIO₄ / 1) acetone, t-BuOH, r.t., 36 h, 2) EtOAc, H₂O, r.t., 16 h

6: 94 percent / Ag₂CO₃, celite / benzene / 0.25 h / Heating

7: 1) Et₃N, MeSO₂Cl, 2) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1) benzene, ice bath, 2 h, 2) benzene, r.t., 2 h

8: 99 percent / 1percent aq. OsO₄, N-methylmorpholine N-oxide / acetone; 2-methyl-propan-2-ol / 24 h / Ambient temperature

9: 70 percent / Bu₄NF / tetrahydrofuran / 1 h / 0 °C

10: 70 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 16 h / Ambient temperature

11: 16 percent / conc. HCl / ethanol / 1 h / Heating

12: 84 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / Ambient temperature

13: 60 percent / diisobutylaluminium hydride / toluene; hexane / 1 h / -75 °C

14: 67 percent / 2-fluoro-1-methylpyridinium tosylate, Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

15: 25 percent / trimethylsilyl trifluoromethanesulfonate / diethyl ether / 16 h / Ambient temperature

16: 70 percent / Bu₄NF / tetrahydrofuran / Ambient temperature

17: 1) 18-crown-6, K₂CO₃ / 1) MeCN, r.t., 2) MeCN, r.t.

18: 70 percent / Bu₄NF / tetrahydrofuran; acetonitrile / 20 h / Ambient temperature

With 2,6-dimethylpyridine; hydrogenchloride; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; adogen 464; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; Celite; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; 1-methyl-2-fluoropyridinium p-toluenesulfonate; methanesulfonyl chloride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; silver carbonate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene;