(2S,3R,4R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-hydroxy-4-phenylpyrrolidine

Base Information

Chemical Name:(2S,3R,4R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-hydroxy-4-phenylpyrrolidine
CAS No.:158177-62-9
Molecular Formula:C₂₈H₃₅NO₆
Molecular Weight:481.589
Hs Code.:

Synonyms:(2S,3R,4R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-hydroxy-4-phenylpyrrolidine

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

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Chemical Property of (2S,3R,4R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-hydroxy-4-phenylpyrrolidine

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Technology Process of (2S,3R,4R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-hydroxy-4-phenylpyrrolidine

There total 5 articles about (2S,3R,4R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-hydroxy-4-phenylpyrrolidine 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: 50.0%

: 100-58-3
phenylmagnesium bromide

: 158177-61-8
(2S,3R)-N-benzoyl-3-tert-butoxycarbonylmethyl-4-oxo proline tert-butyl ester

: 158177-62-9
(2S,3R,4R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-hydroxy-4-phenylpyrrolidine

Guidance literature:: In diethyl ether; 1.) -78 deg C, 2 h, 2.) 0 deg C, 4 h.;
DOI:10.1016/S0040-4020(97)00190-7

Reference yield:

: 31560-19-7
(2S,4R)-1-benzoyl-4-hydroxy-L-proline

: 158177-62-9
(2S,3R,4R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-hydroxy-4-phenylpyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1: 71 percent / dimethylformamide-dineopentylacetal / benzene / Heating

2: 76 percent / RuO₂*xH₂O, NaIO₄ / CCl₄; CHCl₃; H₂O / 6 h / Ambient temperature

3: 99 percent / 5 Angstroem molecular sieves / benzene / 16 h / Ambient temperature

4: 1.) K₂CO₃, 2.) acetic acid / 1.) acetonitrile, room temperature, 120 h, 2.) H₂O, CHCl₃, room temperature, 26 h.

5: 50 percent / diethyl ether / 1.) -78 deg C, 2 h, 2.) 0 deg C, 4 h.

With ruthenium(IV) oxide; sodium periodate; 5A molecular sieve; potassium carbonate; acetic acid; N,N-dimethylformamide dineopentyl acetal; In tetrachloromethane; diethyl ether; chloroform; water; benzene;
DOI:10.1016/S0040-4020(97)00190-7

Reference yield:

: 158177-76-5
N-benzoyl-4-oxo-L-proline tert-butyl ester

: 158177-62-9
(2S,3R,4R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-hydroxy-4-phenylpyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / 5 Angstroem molecular sieves / benzene / 16 h / Ambient temperature

2: 1.) K₂CO₃, 2.) acetic acid / 1.) acetonitrile, room temperature, 120 h, 2.) H₂O, CHCl₃, room temperature, 26 h.

3: 50 percent / diethyl ether / 1.) -78 deg C, 2 h, 2.) 0 deg C, 4 h.

With 5A molecular sieve; potassium carbonate; acetic acid; In diethyl ether; benzene;
DOI:10.1016/S0040-4020(97)00190-7