diethyl (2S,3S)-{[2-(tert-butyldiphenylsilanyloxymethyl)-5-ethoxytetrahydrofuran-3-yl]difluoromethyl}phosphonate

Base Information

Chemical Name:diethyl (2S,3S)-{[2-(tert-butyldiphenylsilanyloxymethyl)-5-ethoxytetrahydrofuran-3-yl]difluoromethyl}phosphonate
CAS No.:496048-28-3
Molecular Formula:C₂₈H₄₁F₂O₆PSi
Molecular Weight:570.686
Hs Code.:

Synonyms:diethyl (2S,3S)-{[2-(tert-butyldiphenylsilanyloxymethyl)-5-ethoxytetrahydrofuran-3-yl]difluoromethyl}phosphonate

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Chemical Property of diethyl (2S,3S)-{[2-(tert-butyldiphenylsilanyloxymethyl)-5-ethoxytetrahydrofuran-3-yl]difluoromethyl}phosphonate

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Technology Process of diethyl (2S,3S)-{[2-(tert-butyldiphenylsilanyloxymethyl)-5-ethoxytetrahydrofuran-3-yl]difluoromethyl}phosphonate

There total 5 articles about diethyl (2S,3S)-{[2-(tert-butyldiphenylsilanyloxymethyl)-5-ethoxytetrahydrofuran-3-yl]difluoromethyl}phosphonate 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: 95.0%

: 122-51-0
orthoformic acid triethyl ester

: {[(2S,3S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-tetrahydro-furan-3-yl]-difluoro-methyl}-phosphonic acid diethyl ester

: 496048-28-3
diethyl (2S,3S)-{[2-(tert-butyldiphenylsilanyloxymethyl)-5-ethoxytetrahydrofuran-3-yl]difluoromethyl}phosphonate

Guidance literature:: With ammonium nitrite; In ethanol; at 80 ℃;
DOI:10.1055/s-2002-34218

Reference yield:

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

: 496048-28-3
diethyl (2S,3S)-{[2-(tert-butyldiphenylsilanyloxymethyl)-5-ethoxytetrahydrofuran-3-yl]difluoromethyl}phosphonate

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

2: 69 percent / BH₃*THF / tetrahydrofuran / 18 h / 0 °C

3: 67 percent / NH₄NO₃ / ethanol / 18 h / 90 °C

With 1H-imidazole; ammonium nitrate; borane-THF; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;
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

: 496048-28-3
diethyl (2S,3S)-{[2-(tert-butyldiphenylsilanyloxymethyl)-5-ethoxytetrahydrofuran-3-yl]difluoromethyl}phosphonate

Guidance literature:: Multi-step reaction with 4 steps

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

2: 93 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

3: 69 percent / BH₃*THF / tetrahydrofuran / 18 h / 0 °C

4: 67 percent / NH₄NO₃ / ethanol / 18 h / 90 °C

With 1H-imidazole; ammonium nitrate; hydrogenchloride; borane-THF; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2003.09.069