(2S,3R,4R)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-difluoromethyl-2-(tert-butyldimethylsiloxymethyl)pyrrolidine

Base Information

Chemical Name:(2S,3R,4R)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-difluoromethyl-2-(tert-butyldimethylsiloxymethyl)pyrrolidine
CAS No.:852616-77-4
Molecular Formula:C₂₄H₃₇F₂NO₅Si
Molecular Weight:485.644
Hs Code.:

Synonyms:(2S,3R,4R)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-difluoromethyl-2-(tert-butyldimethylsiloxymethyl)pyrrolidine

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Chemical Property of (2S,3R,4R)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-difluoromethyl-2-(tert-butyldimethylsiloxymethyl)pyrrolidine

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Technology Process of (2S,3R,4R)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-difluoromethyl-2-(tert-butyldimethylsiloxymethyl)pyrrolidine

There total 13 articles about (2S,3R,4R)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-difluoromethyl-2-(tert-butyldimethylsiloxymethyl)pyrrolidine 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: 75.0%

: (2S,3R,4R)-4-Benzoyloxy-3-difluoromethyl-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 18162-48-6
tert-butyldimethylsilyl chloride

: 852616-77-4
(2S,3R,4R)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-difluoromethyl-2-(tert-butyldimethylsiloxymethyl)pyrrolidine

Guidance literature:: With 1H-imidazole; dmap; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/jo050057+

Reference yield:

: 852616-64-9
tert-butyl (S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,5-dihydro-1H-pyrrole-1-carboxylate

: 852616-77-4
(2S,3R,4R)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-difluoromethyl-2-(tert-butyldimethylsiloxymethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / OsO₄; 4-methylmorpholine N-oxide monohydrate / acetone; H₂O; toluene / 0 - 20 °C

2: 70 percent / DMAP; pyridine / CH₂Cl₂ / -78 - -10 °C

3: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / cooling

4: 83 percent / HMPT; Zn / tetrahydrofuran / 0.5 h / Heating

5: 54 percent / hydrogen / Pd(OH)2/C / dioxane / 31 h / 76000 Torr

6: 280 mg / TBAF / tetrahydrofuran / 0 - 20 °C

7: 75 percent / DMAP; imidazole / CH₂Cl₂ / 0 - 20 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; osmium(VIII) oxide; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; 4-methylmorpholine 4-oxide monohydrate; zinc; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetone; toluene;
DOI:10.1021/jo050057+

Reference yield:

: 852616-66-1
tert-butyl (2R,3R,4S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-3,4-dihydroxypyrrolidine-1-carboxylate

: 852616-77-4
(2S,3R,4R)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-difluoromethyl-2-(tert-butyldimethylsiloxymethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / DMAP; pyridine / CH₂Cl₂ / -78 - -10 °C

2: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / cooling

3: 83 percent / HMPT; Zn / tetrahydrofuran / 0.5 h / Heating

4: 54 percent / hydrogen / Pd(OH)2/C / dioxane / 31 h / 76000 Torr

5: 280 mg / TBAF / tetrahydrofuran / 0 - 20 °C

6: 75 percent / DMAP; imidazole / CH₂Cl₂ / 0 - 20 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; zinc; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1021/jo050057+