(4S,5S)-5-{[tert-butyl(diphenyl)silyl]methyl}-4-[(diethoxyphosphorothioyl)(difluoro)methyl]tetrahydrofuran-2-yl acetate

Base Information

Chemical Name:(4S,5S)-5-{[tert-butyl(diphenyl)silyl]methyl}-4-[(diethoxyphosphorothioyl)(difluoro)methyl]tetrahydrofuran-2-yl acetate
CAS No.:496048-33-0
Molecular Formula:C₂₈H₃₉F₂O₆PSSi
Molecular Weight:600.736
Hs Code.:

Synonyms:(4S,5S)-5-{[tert-butyl(diphenyl)silyl]methyl}-4-[(diethoxyphosphorothioyl)(difluoro)methyl]tetrahydrofuran-2-yl acetate

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Chemical Property of (4S,5S)-5-{[tert-butyl(diphenyl)silyl]methyl}-4-[(diethoxyphosphorothioyl)(difluoro)methyl]tetrahydrofuran-2-yl acetate

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Technology Process of (4S,5S)-5-{[tert-butyl(diphenyl)silyl]methyl}-4-[(diethoxyphosphorothioyl)(difluoro)methyl]tetrahydrofuran-2-yl acetate

There total 7 articles about (4S,5S)-5-{[tert-butyl(diphenyl)silyl]methyl}-4-[(diethoxyphosphorothioyl)(difluoro)methyl]tetrahydrofuran-2-yl acetate 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: 96.0%

: 108-24-7
acetic anhydride

: (2S,3S)-{[2-(tert-butyldiphenylsilanyloxymethyl)-5-hydroxytetrahydrofuran-3-yl]difluoromethyl}phosphonothioic acid O,O-diethyl ester

: 496048-33-0
(4S,5S)-5-{[tert-butyl(diphenyl)silyl]methyl}-4-[(diethoxyphosphorothioyl)(difluoro)methyl]tetrahydrofuran-2-yl acetate

Guidance literature:: With dmap; In pyridine; at 20 ℃; for 24h;
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

: 496048-33-0
(4S,5S)-5-{[tert-butyl(diphenyl)silyl]methyl}-4-[(diethoxyphosphorothioyl)(difluoro)methyl]tetrahydrofuran-2-yl acetate

Guidance literature:: Multi-step reaction with 4 steps

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

2: 84 percent / Lawesson's reagent / toluene / 2 h / 120 °C

3: 92 percent / BH₃*THF / tetrahydrofuran / 12 h / cooling

4: 96 percent / dimethylaminopyridine / pyridine / 24 h / 20 °C

With Lawessons reagent; 1H-imidazole; dmap; borane-THF; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2003.09.069

Reference yield:

: 496048-30-7
(2S,3S)-{[2-(tert-butyldiphenylsilanyloxymethyl)-5-oxotetrahydrofuran-3-yl]difluoromethyl}phosphonothioic acid O,O-diethyl ester

: 496048-33-0
(4S,5S)-5-{[tert-butyl(diphenyl)silyl]methyl}-4-[(diethoxyphosphorothioyl)(difluoro)methyl]tetrahydrofuran-2-yl acetate

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / BH₃*THF / tetrahydrofuran / 12 h / cooling

2: 96 percent / dimethylaminopyridine / pyridine / 24 h / 20 °C

With dmap; borane-THF; In tetrahydrofuran; pyridine;
DOI:10.1016/j.tet.2003.09.069