tert-butyl (2R,3R,4R)-4-azido-2-tert-butyldiphenylsilyloxymethyl-3-hydroxy-pyrrolidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (2R,3R,4R)-4-azido-2-tert-butyldiphenylsilyloxymethyl-3-hydroxy-pyrrolidine-1-carboxylate
CAS No.:194737-65-0
Molecular Formula:C₂₆H₃₆N₄O₄Si
Molecular Weight:496.682
Hs Code.:

Synonyms:tert-butyl (2R,3R,4R)-4-azido-2-tert-butyldiphenylsilyloxymethyl-3-hydroxy-pyrrolidine-1-carboxylate

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Chemical Property of tert-butyl (2R,3R,4R)-4-azido-2-tert-butyldiphenylsilyloxymethyl-3-hydroxy-pyrrolidine-1-carboxylate

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Technology Process of tert-butyl (2R,3R,4R)-4-azido-2-tert-butyldiphenylsilyloxymethyl-3-hydroxy-pyrrolidine-1-carboxylate

There total 6 articles about tert-butyl (2R,3R,4R)-4-azido-2-tert-butyldiphenylsilyloxymethyl-3-hydroxy-pyrrolidine-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: 59.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 194737-57-0
tert-butyl (2R,3R,4R)-4-azido-3-hydroxy-2-hydroxymethylpyrrolidine-1-carboxylate

: 194737-65-0
tert-butyl (2R,3R,4R)-4-azido-2-tert-butyldiphenylsilyloxymethyl-3-hydroxy-pyrrolidine-1-carboxylate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 36h; Ambient temperature;
DOI:10.1016/S0957-4166(97)00261-9

Reference yield:

: 134107-65-6
(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one

: 194737-65-0
tert-butyl (2R,3R,4R)-4-azido-2-tert-butyldiphenylsilyloxymethyl-3-hydroxy-pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 87 percent / K₂CO₃, t-BuOOH / dimethylformamide; various solvent(s) / 0.5 h / Ambient temperature

2: BH₃*THF / tetrahydrofuran / 16 h / 0 °C

3: H₂ / 10percent Pd/C / ethyl acetate / 18 h / 3800 Torr

4: 73 percent / NaN₃, NH₄Cl / methanol; H₂O / 72 h / Heating

5: 59 percent / imidazole / dimethylformamide / 36 h / Ambient temperature

With 1H-imidazole; tert.-butylhydroperoxide; sodium azide; borane-THF; hydrogen; potassium carbonate; ammonium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(97)00261-9

Reference yield:

: 103201-79-2,1820583-17-2
(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

: 194737-65-0
tert-butyl (2R,3R,4R)-4-azido-2-tert-butyldiphenylsilyloxymethyl-3-hydroxy-pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / PhSO₂Me, KH / tetrahydrofuran / 2 h / Ambient temperature

2: 87 percent / K₂CO₃, t-BuOOH / dimethylformamide; various solvent(s) / 0.5 h / Ambient temperature

3: BH₃*THF / tetrahydrofuran / 16 h / 0 °C

4: H₂ / 10percent Pd/C / ethyl acetate / 18 h / 3800 Torr

5: 73 percent / NaN₃, NH₄Cl / methanol; H₂O / 72 h / Heating

6: 59 percent / imidazole / dimethylformamide / 36 h / Ambient temperature

With 1H-imidazole; tert.-butylhydroperoxide; sodium azide; borane-THF; methylphenylsulfonate; hydrogen; potassium hydride; potassium carbonate; ammonium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(97)00261-9