benzyl (2R,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-hydroxypyrrolidine-1-carboxylate

Base Information

Chemical Name:benzyl (2R,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-hydroxypyrrolidine-1-carboxylate
CAS No.:832133-02-5
Molecular Formula:C₂₀H₃₂FNO₄Si
Molecular Weight:397.562
Hs Code.:

Synonyms:benzyl (2R,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-hydroxypyrrolidine-1-carboxylate

Suppliers and Price of benzyl (2R,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-hydroxypyrrolidine-1-carboxylate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of benzyl (2R,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-hydroxypyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of benzyl (2R,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-hydroxypyrrolidine-1-carboxylate

There total 5 articles about benzyl (2R,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-hydroxypyrrolidine-1-carboxylate 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: 81.0%

: 832133-00-3
(5S,3S)-N-benzyloxycarbonyl-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-pyrrolidone

: 832133-02-5
benzyl (2R,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-hydroxypyrrolidine-1-carboxylate

: benzyl (2S,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-hydroxypyrrolidine-1-carboxylate

Guidance literature:: With lithium triethylborohydride; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1016/j.bmc.2004.09.040

Reference yield:

: methyl (2S)-N-tert-butoxycarbonyl-4-difluoromethylpyroglutamate

: 832133-02-5
benzyl (2R,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-hydroxypyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 75 percent / Et₃N / tetrahydrofuran / 20 °C

2.1: 84 percent / H₂ / Pd on BaSO₄ / dioxane / 24 h / 20 °C / 760 Torr

3.1: trifluoroacetic acid / CH₂Cl₂ / -78 - 20 °C

3.2: NaBH₄ / methanol / 1.5 h / 0 °C

3.3: 67 percent / DMAP; imidazole / CH₂Cl₂; dimethylformamide / 20 °C

4.1: 93 percent / LHMDS / tetrahydrofuran / 0.17 h / -78 °C

5.1: 81 percent / LiBEt₃H / tetrahydrofuran / 1 h / -78 °C

With hydrogen; lithium triethylborohydride; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on barium sulfate; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1016/j.bmc.2004.09.040

Reference yield:

: 832132-91-9
methyl (2S)-N-tert-butoxycarbonyl-4-[(Z)-fluoromethylidene]pyroglutamate

: 832133-02-5
benzyl (2R,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-hydroxypyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 84 percent / H₂ / Pd on BaSO₄ / dioxane / 24 h / 20 °C / 760 Torr

2.1: trifluoroacetic acid / CH₂Cl₂ / -78 - 20 °C

2.2: NaBH₄ / methanol / 1.5 h / 0 °C

2.3: 67 percent / DMAP; imidazole / CH₂Cl₂; dimethylformamide / 20 °C

3.1: 93 percent / LHMDS / tetrahydrofuran / 0.17 h / -78 °C

4.1: 81 percent / LiBEt₃H / tetrahydrofuran / 1 h / -78 °C

With hydrogen; lithium triethylborohydride; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on barium sulfate; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1016/j.bmc.2004.09.040