(2S,3R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-trifluoromethanesulfonyloxy-<4,5>-dehydropyrrolidine

Base Information

Chemical Name:(2S,3R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-trifluoromethanesulfonyloxy-<4,5>-dehydropyrrolidine
CAS No.:169774-62-3
Molecular Formula:C₂₃H₂₈F₃NO₈S
Molecular Weight:535.538
Hs Code.:

Synonyms:(2S,3R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-trifluoromethanesulfonyloxy-<4,5>-dehydropyrrolidine

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Chemical Property of (2S,3R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-trifluoromethanesulfonyloxy-<4,5>-dehydropyrrolidine

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Technology Process of (2S,3R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-trifluoromethanesulfonyloxy-<4,5>-dehydropyrrolidine

There total 5 articles about (2S,3R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-trifluoromethanesulfonyloxy-<4,5>-dehydropyrrolidine 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:

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

: 169774-62-3
(2S,3R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-trifluoromethanesulfonyloxy-<4,5>-dehydropyrrolidine

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: 1.) LiHMDS, 2.) N,N'-dimethyl-N,N'-propylene urea / 1.) THF, -78 deg C, 40 min, 2.) THF, room temperature, 16 h.

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; ruthenium(IV) oxide; sodium periodate; 5A molecular sieve; potassium carbonate; acetic acid; N,N-dimethylformamide dineopentyl acetal; lithium hexamethyldisilazane; In tetrachloromethane; 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

: 169774-62-3
(2S,3R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-trifluoromethanesulfonyloxy-<4,5>-dehydropyrrolidine

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: 1.) LiHMDS, 2.) N,N'-dimethyl-N,N'-propylene urea / 1.) THF, -78 deg C, 40 min, 2.) THF, room temperature, 16 h.

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 5A molecular sieve; potassium carbonate; acetic acid; lithium hexamethyldisilazane; In benzene;
DOI:10.1016/S0040-4020(97)00190-7

Reference yield:

: 158177-75-4
N-benzoyl-trans-4-hydroxy-L-proline tert-butyl ester

: 169774-62-3
(2S,3R)-N-benzoyl-2-tert-butoxycarbonyl-3-tert-butoxycarbonylmethyl-4-trifluoromethanesulfonyloxy-<4,5>-dehydropyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1: 76 percent / RuO₂*xH₂O, NaIO₄ / CCl₄; CHCl₃; H₂O / 6 h / Ambient temperature

2: 99 percent / 5 Angstroem molecular sieves / benzene / 16 h / Ambient temperature

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

4: 1.) LiHMDS, 2.) N,N'-dimethyl-N,N'-propylene urea / 1.) THF, -78 deg C, 40 min, 2.) THF, room temperature, 16 h.

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; ruthenium(IV) oxide; sodium periodate; 5A molecular sieve; potassium carbonate; acetic acid; lithium hexamethyldisilazane; In tetrachloromethane; chloroform; water; benzene;
DOI:10.1016/S0040-4020(97)00190-7