3-Fluoro-benzoic acid (2R,3aR,4R,6R,6aS)-6-(1-hydroxy-ethyl)-6-hydroxymethyl-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester

Base Information

Chemical Name:3-Fluoro-benzoic acid (2R,3aR,4R,6R,6aS)-6-(1-hydroxy-ethyl)-6-hydroxymethyl-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester
CAS No.:906640-46-8
Molecular Formula:C₂₁H₂₁FO₇
Molecular Weight:404.392
Hs Code.:

Synonyms:3-Fluoro-benzoic acid (2R,3aR,4R,6R,6aS)-6-(1-hydroxy-ethyl)-6-hydroxymethyl-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester

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Chemical Property of 3-Fluoro-benzoic acid (2R,3aR,4R,6R,6aS)-6-(1-hydroxy-ethyl)-6-hydroxymethyl-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester

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Technology Process of 3-Fluoro-benzoic acid (2R,3aR,4R,6R,6aS)-6-(1-hydroxy-ethyl)-6-hydroxymethyl-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester

There total 5 articles about 3-Fluoro-benzoic acid (2R,3aR,4R,6R,6aS)-6-(1-hydroxy-ethyl)-6-hydroxymethyl-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-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: 50.0%

: 906640-40-2
3-Fluoro-benzoic acid (2R,3aR,4R,6R,6aR)-2-(2-bromo-phenyl)-6-(diphenyl-vinyl-silanyloxymethyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester

: 3-Fluoro-benzoic acid (2R,3aR,4R,6R,6aR)-6-hydroxymethyl-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester

: 906640-46-8
3-Fluoro-benzoic acid (2R,3aR,4R,6R,6aS)-6-(1-hydroxy-ethyl)-6-hydroxymethyl-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester

Guidance literature:: 3-Fluoro-benzoic acid (2R,3aR,4R,6R,6aR)-2-(2-bromo-phenyl)-6-(diphenyl-vinyl-silanyloxymethyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester; With air; triethyl borane; tri-n-butyl-tin hydride; In hexane; benzene; at 20 ℃;

With potassium hydrogen bifluoride; 3-chloro-benzenecarboperoxoic acid; In N,N-dimethyl-formamide; at 50 ℃; for 2.5h;
DOI:10.1021/ol061162o

Reference yield:

: 906640-39-9
3-Fluoro-benzoic acid (2R,3aR,4R,6R,6aR)-2-(2-bromo-phenyl)-6-hydroxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester

: 906640-46-8
3-Fluoro-benzoic acid (2R,3aR,4R,6R,6aS)-6-(1-hydroxy-ethyl)-6-hydroxymethyl-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 98 percent / DMAP; Et₃N / toluene / 1.5 h / 20 °C

2.1: Bu₃SnH; Et₃B; air / benzene; hexane / 20 °C

2.2: 50 percent / KHF₂; m-CPBA / dimethylformamide / 2.5 h / 50 °C

With dmap; air; triethyl borane; tri-n-butyl-tin hydride; triethylamine; In hexane; toluene; benzene; 2.2: Tamao oxidation;
DOI:10.1021/ol061162o

Reference yield:

: (2R,3aR,6R,6aR)-2-(2-Bromo-phenyl)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol

: 906640-46-8
3-Fluoro-benzoic acid (2R,3aR,4R,6R,6aS)-6-(1-hydroxy-ethyl)-6-hydroxymethyl-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 75 percent / PPh₃; diisopropyl azodicarboxylate / CH₂Cl₂ / 0 - 20 °C

2.1: 89 percent / NH₄F / ethanol; methanol / 48 h / 20 °C

3.1: 98 percent / DMAP; Et₃N / toluene / 1.5 h / 20 °C

4.1: Bu₃SnH; Et₃B; air / benzene; hexane / 20 °C

4.2: 50 percent / KHF₂; m-CPBA / dimethylformamide / 2.5 h / 50 °C

With dmap; ammonium fluoride; air; triethyl borane; di-isopropyl azodicarboxylate; tri-n-butyl-tin hydride; triethylamine; triphenylphosphine; In methanol; ethanol; hexane; dichloromethane; toluene; benzene; 1.1: Mitsunobu reaction / 4.2: Tamao oxidation;
DOI:10.1021/ol061162o