(+/-)-(1S,2R/S,5R,6S*)-1-(tert-Butyldimethylsilyl)oxy-6-<5-(tert-butyldimethylsilyl)oxy-2-methoxyphenyl>-2-fluoro-3,7-dioxabicyclo<3.3.0>octane

Base Information

Chemical Name:(+/-)-(1S*,2R*/S*,5R*,6S*)-1-(tert-Butyldimethylsilyl)oxy-6-<5-(tert-butyldimethylsilyl)oxy-2-methoxyphenyl>-2-fluoro-3,7-dioxabicyclo<3.3.0>octane
CAS No.:142677-31-4
Molecular Formula:C₂₅H₄₃FO₅Si₂
Molecular Weight:498.783
Hs Code.:

(+/-)-(1S*,2R*/S*,5R*,6S*)-1-(tert-Butyldimethylsilyl)oxy-6-<5-(tert-butyldimethylsilyl)oxy-2-methoxyphenyl>-2-fluoro-3,7-dioxabicyclo<3.3.0>octane

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Chemical Property of (+/-)-(1S*,2R*/S*,5R*,6S*)-1-(tert-Butyldimethylsilyl)oxy-6-<5-(tert-butyldimethylsilyl)oxy-2-methoxyphenyl>-2-fluoro-3,7-dioxabicyclo<3.3.0>octane

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Technology Process of (+/-)-(1S*,2R*/S*,5R*,6S*)-1-(tert-Butyldimethylsilyl)oxy-6-<5-(tert-butyldimethylsilyl)oxy-2-methoxyphenyl>-2-fluoro-3,7-dioxabicyclo<3.3.0>octane

There total 25 articles about (+/-)-(1S*,2R*/S*,5R*,6S*)-1-(tert-Butyldimethylsilyl)oxy-6-<5-(tert-butyldimethylsilyl)oxy-2-methoxyphenyl>-2-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: 70.0%

: 142677-30-3,142760-48-3
(+/-)-(1S*,2R*/S*,5R*,6S*)-1-(tert-Butyldimethylsilyl)oxy-6-<5-(tert-butyldimethylsilyl)oxy-2-methoxyphenyl>-2-hydroxy-3,7-dioxabicyclo<3.3.0>octane

: 142677-31-4,142759-15-7
(+/-)-(1S*,2R*/S*,5R*,6S*)-1-(tert-Butyldimethylsilyl)oxy-6-<5-(tert-butyldimethylsilyl)oxy-2-methoxyphenyl>-2-fluoro-3,7-dioxabicyclo<3.3.0>octane

Guidance literature:: With 1-methyl-2-fluoropyridinium p-toluenesulfonate; triethylamine; In dichloromethane; for 3h; Ambient temperature;

Reference yield:

: 1194-98-5
2,5-Dihydroxybenzaldehyde

: 142677-31-4,142759-15-7
(+/-)-(1S*,2R*/S*,5R*,6S*)-1-(tert-Butyldimethylsilyl)oxy-6-<5-(tert-butyldimethylsilyl)oxy-2-methoxyphenyl>-2-fluoro-3,7-dioxabicyclo<3.3.0>octane

Guidance literature:: Multi-step reaction with 15 steps

1: 64 percent / p-TsOH / CH₂Cl₂ / 12 h / Heating

2: 83 percent / NaOH, PhCH₂(n-Bu)3NBr / CH₂Cl₂; H₂O / 16 h / Ambient temperature

3: 40 percent / LDA / tetrahydrofuran / 3 h / -75 °C

4: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 75 percent / LiAlH₄ / diethyl ether / 0.5 h / -10 °C

6: OsO₄, N-methylmorpholine oxide (NMO) / acetone; H₂O; 2-methyl-propan-2-ol / 24 h / Ambient temperature

7: 1.) NaIO₄, 2.) Ag₂CO₃ celite / 1.) aq. EtOAc, 2.) benzene, 30 min, reflux

8: Et₃N / benzene / 0.5 h / Ambient temperature

9: 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene / 0.5 h / Ambient temperature

10: 88 percent / OsO₄, N-methylmorpholine oxide (NMO) / acetone; H₂O; 2-methyl-propan-2-ol / 12 h / Ambient temperature

11: 83 percent / tetra-n-butylammonium fluoride (TBAF) / tetrahydrofuran / 2 h / 0 °C

12: 56 percent / p-TsOH / CH₂Cl₂ / 72 h / Ambient temperature

13: 89 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / Ambient temperature

14: 82 percent / diisobutyl aluminium hydride (DIBAL-H) / toluene / 1 h / -75 °C

15: 70 percent / 2-fluoro-1-methylpyridinium tosylate, Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

With 2,6-dimethylpyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; benzyl tri-n-butylammonium bromide; diisobutylaluminium hydride; 1-methyl-2-fluoropyridinium p-toluenesulfonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; silver carbonate; 1,5-Diazabicyclo[5.4.0]undec-5-ene; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene;

Reference yield:

: 142677-24-5
2-methoxy-5-(methoxymethoxy)benzaldehyde

: 142677-31-4,142759-15-7
(+/-)-(1S*,2R*/S*,5R*,6S*)-1-(tert-Butyldimethylsilyl)oxy-6-<5-(tert-butyldimethylsilyl)oxy-2-methoxyphenyl>-2-fluoro-3,7-dioxabicyclo<3.3.0>octane

Guidance literature:: Multi-step reaction with 13 steps

1: 40 percent / LDA / tetrahydrofuran / 3 h / -75 °C

2: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 75 percent / LiAlH₄ / diethyl ether / 0.5 h / -10 °C

4: OsO₄, N-methylmorpholine oxide (NMO) / acetone; H₂O; 2-methyl-propan-2-ol / 24 h / Ambient temperature

5: 1.) NaIO₄, 2.) Ag₂CO₃ celite / 1.) aq. EtOAc, 2.) benzene, 30 min, reflux

6: Et₃N / benzene / 0.5 h / Ambient temperature

7: 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene / 0.5 h / Ambient temperature

8: 88 percent / OsO₄, N-methylmorpholine oxide (NMO) / acetone; H₂O; 2-methyl-propan-2-ol / 12 h / Ambient temperature

9: 83 percent / tetra-n-butylammonium fluoride (TBAF) / tetrahydrofuran / 2 h / 0 °C

10: 56 percent / p-TsOH / CH₂Cl₂ / 72 h / Ambient temperature

11: 89 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / Ambient temperature

12: 82 percent / diisobutyl aluminium hydride (DIBAL-H) / toluene / 1 h / -75 °C

13: 70 percent / 2-fluoro-1-methylpyridinium tosylate, Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 1-methyl-2-fluoropyridinium p-toluenesulfonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; silver carbonate; 1,5-Diazabicyclo[5.4.0]undec-5-ene; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene;