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

Base Information

Chemical Name:benzyl (2R,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-difluoromethyl-2-hydroxypyrrolidine-1-carboxylate
CAS No.:681283-28-3
Molecular Formula:C₂₀H₃₁F₂NO₄Si
Molecular Weight:415.553
Hs Code.:

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

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

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

There total 11 articles about benzyl (2R,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-difluoromethyl-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:

: 1499-56-5,775275-31-5,790644-51-8,754962-86-2
(R)-4-hydroxy-L-proline ethyl ester

: 681283-28-3
benzyl (2R,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-difluoromethyl-2-hydroxypyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 15.715 g / DMAP; Et₃N / CH₂Cl₂ / 20 °C

2.1: 11 g / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 °C

3.1: HMPT / tetrahydrofuran / 0.5 h / 20 °C

3.2: 50 percent / Zn; HMPT / tetrahydrofuran / 0.33 h / Heating

4.1: 94 percent / H₂ / Pd/C / ethanol / 20 °C / 760 Torr

5.1: 68 percent / aq. NaIO₄ / RuO₂*xH₂O / ethyl acetate / 30 h / 20 °C

6.1: CF₃COOH / CH₂Cl₂ / 20 °C

7.1: NaBH₄ / methanol / 2 h / 0 °C

8.1: 587 mg / DMAP; imidazole / CH₂Cl₂; dimethylformamide / 20 °C

9.1: LHMDS / tetrahydrofuran / 0.17 h / -78 °C

9.2: 83 percent / tetrahydrofuran / 0.17 h / -78 °C

10.1: 79.3 percent / LiBEt₃H / tetrahydrofuran / 3.5 h / -78 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; hydrogen; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; ruthenium(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 2.1: Swern oxidation;
DOI:10.1055/s-2004-815932

Reference yield:

: 74844-91-0
1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

: 681283-28-3
benzyl (2R,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-difluoromethyl-2-hydroxypyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 11 g / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 °C

2.1: HMPT / tetrahydrofuran / 0.5 h / 20 °C

2.2: 50 percent / Zn; HMPT / tetrahydrofuran / 0.33 h / Heating

3.1: 94 percent / H₂ / Pd/C / ethanol / 20 °C / 760 Torr

4.1: 68 percent / aq. NaIO₄ / RuO₂*xH₂O / ethyl acetate / 30 h / 20 °C

5.1: CF₃COOH / CH₂Cl₂ / 20 °C

6.1: NaBH₄ / methanol / 2 h / 0 °C

7.1: 587 mg / DMAP; imidazole / CH₂Cl₂; dimethylformamide / 20 °C

8.1: LHMDS / tetrahydrofuran / 0.17 h / -78 °C

8.2: 83 percent / tetrahydrofuran / 0.17 h / -78 °C

9.1: 79.3 percent / LiBEt₃H / tetrahydrofuran / 3.5 h / -78 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; hydrogen; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; ruthenium(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: Swern oxidation;
DOI:10.1055/s-2004-815932

Reference yield:

: 102195-80-2
(S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

: 681283-28-3
benzyl (2R,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-difluoromethyl-2-hydroxypyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: HMPT / tetrahydrofuran / 0.5 h / 20 °C

1.2: 50 percent / Zn; HMPT / tetrahydrofuran / 0.33 h / Heating

2.1: 94 percent / H₂ / Pd/C / ethanol / 20 °C / 760 Torr

3.1: 68 percent / aq. NaIO₄ / RuO₂*xH₂O / ethyl acetate / 30 h / 20 °C

4.1: CF₃COOH / CH₂Cl₂ / 20 °C

5.1: NaBH₄ / methanol / 2 h / 0 °C

6.1: 587 mg / DMAP; imidazole / CH₂Cl₂; dimethylformamide / 20 °C

7.1: LHMDS / tetrahydrofuran / 0.17 h / -78 °C

7.2: 83 percent / tetrahydrofuran / 0.17 h / -78 °C

8.1: 79.3 percent / LiBEt₃H / tetrahydrofuran / 3.5 h / -78 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; sodium periodate; hydrogen; lithium triethylborohydride; trifluoroacetic acid; lithium hexamethyldisilazane; ruthenium(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1055/s-2004-815932