1α-(tert-butyldimethylsilyl)oxy-6α-<4-(tert-butyldimethylsilyl)oxy-2-methoxy-5-(2-methoxyethoxy)phenyl>-2α/β-fluoro-3,7-dioxabicyclo<3.3.0>octane

Base Information

Chemical Name:1α-(tert-butyldimethylsilyl)oxy-6α-<4-(tert-butyldimethylsilyl)oxy-2-methoxy-5-(2-methoxyethoxy)phenyl>-2α/β-fluoro-3,7-dioxabicyclo<3.3.0>octane
CAS No.:142216-53-3
Molecular Formula:C₂₈H₄₉FO₇Si₂
Molecular Weight:572.862
Hs Code.:

1α-(tert-butyldimethylsilyl)oxy-6α-<4-(tert-butyldimethylsilyl)oxy-2-methoxy-5-(2-methoxyethoxy)phenyl>-2α/β-fluoro-3,7-dioxabicyclo<3.3.0>octane

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Chemical Property of 1α-(tert-butyldimethylsilyl)oxy-6α-<4-(tert-butyldimethylsilyl)oxy-2-methoxy-5-(2-methoxyethoxy)phenyl>-2α/β-fluoro-3,7-dioxabicyclo<3.3.0>octane

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Technology Process of 1α-(tert-butyldimethylsilyl)oxy-6α-<4-(tert-butyldimethylsilyl)oxy-2-methoxy-5-(2-methoxyethoxy)phenyl>-2α/β-fluoro-3,7-dioxabicyclo<3.3.0>octane

There total 24 articles about 1α-(tert-butyldimethylsilyl)oxy-6α-<4-(tert-butyldimethylsilyl)oxy-2-methoxy-5-(2-methoxyethoxy)phenyl>-2α/β-fluoro-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%

: 142216-55-5,142291-85-8
1α-(tert-butyldimethylsilyl)oxy-6α-<4-(tert-butyldimethylsilyl)oxy-2-methoxy-5-(2-methoxyethoxy)phenyl>-2α/β-hydroxy-3,7-dioxabicyclo<3.3.0>octane

: 142216-53-3,142291-83-6
1α-(tert-butyldimethylsilyl)oxy-6α-<4-(tert-butyldimethylsilyl)oxy-2-methoxy-5-(2-methoxyethoxy)phenyl>-2α/β-fluoro-3,7-dioxabicyclo<3.3.0>octane

Guidance literature:: With 1-methyl-2-fluoropyridinium p-toluenesulfonate; triethylamine; In dichloromethane; for 2h; Ambient temperature;

Reference yield:

: 142206-55-1
3-benzyloxy-4-(2-methoxyethoxy)phenol

: 142216-53-3,142291-83-6
1α-(tert-butyldimethylsilyl)oxy-6α-<4-(tert-butyldimethylsilyl)oxy-2-methoxy-5-(2-methoxyethoxy)phenyl>-2α/β-fluoro-3,7-dioxabicyclo<3.3.0>octane

Guidance literature:: Multi-step reaction with 15 steps

1: 99 percent / NaH / tetrahydrofuran; paraffin / 48 h / Ambient temperature

2: 83 percent / POCl₃ / 1 h / 60 °C

3: 47 percent / i-Pr₂NLi / tetrahydrofuran / 2 h / -75 °C

4: 86 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / Ambient temperature

5: 67 percent / LiAlH₄ / diethyl ether / 0.5 h / -10 °C

6: 1) 2percent aq. OsO₄, N-methylmorpholine N-oxide, 2) NaIO₄ / 1) acetone, t-BuOH, r.t., 16 h, 2) EtOAc, H₂O, r.t., 2 h

7: 93 percent / Ag₂CO₃, celite / benzene / 0.5 h / Heating

8: 1) Et₃N, MeSO₂Cl, 2) Et₃N / 1) benzene, r.t., 2 h, 2) benzene, r.t., 16 h

9: 98 percent / N-methylmorpholine N-oxide, 2percent aq. OsO₄ / acetone; 2-methyl-propan-2-ol / 24 h / Ambient temperature

10: 94 percent / Bu₄NF / tetrahydrofuran / 1 h / 0 °C

11: 57 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 16 h / Ambient temperature

12: 82 percent / H₂ / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature

13: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

14: 69 percent / DIBAL-H / toluene / 0.5 h / -75 °C

15: 74 percent / 2-fluoro-1-methylpyridinium tosylate, Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; Celite; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; 1-methyl-2-fluoropyridinium p-toluenesulfonate; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; silver carbonate; lithium diisopropyl amide; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; paraffin; tert-butyl alcohol; benzene;

Reference yield:

: 2-benzyloxy-4-methoxy-1-(2-methoxyethoxy)benzene

: 142216-53-3,142291-83-6
1α-(tert-butyldimethylsilyl)oxy-6α-<4-(tert-butyldimethylsilyl)oxy-2-methoxy-5-(2-methoxyethoxy)phenyl>-2α/β-fluoro-3,7-dioxabicyclo<3.3.0>octane

Guidance literature:: Multi-step reaction with 14 steps

1: 83 percent / POCl₃ / 1 h / 60 °C

2: 47 percent / i-Pr₂NLi / tetrahydrofuran / 2 h / -75 °C

3: 86 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / Ambient temperature

4: 67 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., 16 h, 2) EtOAc, H₂O, r.t., 2 h

6: 93 percent / Ag₂CO₃, celite / benzene / 0.5 h / Heating

7: 1) Et₃N, MeSO₂Cl, 2) Et₃N / 1) benzene, r.t., 2 h, 2) benzene, r.t., 16 h

8: 98 percent / N-methylmorpholine N-oxide, 2percent aq. OsO₄ / acetone; 2-methyl-propan-2-ol / 24 h / Ambient temperature

9: 94 percent / Bu₄NF / tetrahydrofuran / 1 h / 0 °C

10: 57 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 16 h / Ambient temperature

11: 82 percent / H₂ / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature

12: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

13: 69 percent / DIBAL-H / toluene / 0.5 h / -75 °C

14: 74 percent / 2-fluoro-1-methylpyridinium tosylate, Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; Celite; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; 1-methyl-2-fluoropyridinium p-toluenesulfonate; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; silver carbonate; lithium diisopropyl amide; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; tert-butyl alcohol; benzene;