(2S,3S)-[(2-benzyloxymethyl-5-ethoxytetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl ester

Base Information

Chemical Name:(2S,3S)-[(2-benzyloxymethyl-5-ethoxytetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl ester
CAS No.:675147-58-7
Molecular Formula:C₁₉H₂₉F₂O₅PS
Molecular Weight:438.473
Hs Code.:

Synonyms:(2S,3S)-[(2-benzyloxymethyl-5-ethoxytetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl ester

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Chemical Property of (2S,3S)-[(2-benzyloxymethyl-5-ethoxytetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl ester

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Technology Process of (2S,3S)-[(2-benzyloxymethyl-5-ethoxytetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl ester

There total 5 articles about (2S,3S)-[(2-benzyloxymethyl-5-ethoxytetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl 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: 85.0%

: 122-51-0
orthoformic acid triethyl ester

: (2S,3S)-[(2-benzyloxymethyl-5-hydroxytetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl ester

: 675147-58-7
(2S,3S)-[(2-benzyloxymethyl-5-ethoxytetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl ester

Guidance literature:: With ammonium nitrate; In ethanol; Heating;
DOI:10.1016/j.tet.2003.09.069

Reference yield:

: 496048-25-0
(2S,3S)-[difluoro(2-hydroxymethyl-5-oxotetrahydrofuran-3-yl)methyl]phosphonic acid diethyl ester

: 675147-58-7
(2S,3S)-[(2-benzyloxymethyl-5-ethoxytetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / CF₃SO₃H / CH₂Cl₂; petroleum ether / 1 h / 0 °C

2: 76 percent / Lawesson's reagent / toluene / Heating

3: 62 percent / BH₃*THF / tetrahydrofuran / cooling

4: 85 percent / NH₄NO₃ / ethanol / Heating

With Lawessons reagent; ammonium nitrate; borane-THF; trifluorormethanesulfonic acid; In tetrahydrofuran; ethanol; dichloromethane; toluene; Petroleum ether;
DOI:10.1016/j.tet.2003.09.069

Reference yield:

: 496048-24-9
tert-butyl 2,3-dideoxy-3-[(diethoxyphosphoryl)difluoromethyl]-4,5-O-(1-methylethylidene)-D-glyceropentonate

: 675147-58-7
(2S,3S)-[(2-benzyloxymethyl-5-ethoxytetrahydrofuran-3-yl)difluoromethyl]phosphonothioic acid O,O-diethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 50 percent / conc. HCl / ethanol / 2 h / 20 °C

2: 84 percent / CF₃SO₃H / CH₂Cl₂; petroleum ether / 1 h / 0 °C

3: 76 percent / Lawesson's reagent / toluene / Heating

4: 62 percent / BH₃*THF / tetrahydrofuran / cooling

5: 85 percent / NH₄NO₃ / ethanol / Heating

With Lawessons reagent; ammonium nitrate; hydrogenchloride; borane-THF; trifluorormethanesulfonic acid; In tetrahydrofuran; ethanol; dichloromethane; toluene; Petroleum ether;
DOI:10.1016/j.tet.2003.09.069