(2R,5R)-5-<4-(benzyloxy)butyl>-N-<(benzyloxy)carbonyl>-2-<4-(p-toluenesulfonyloxy)butyl>pyrrolidine

Base Information

Chemical Name:(2R,5R)-5-<4-(benzyloxy)butyl>-N-<(benzyloxy)carbonyl>-2-<4-(p-toluenesulfonyloxy)butyl>pyrrolidine
CAS No.:142841-52-9
Molecular Formula:C₃₄H₄₃NO₆S
Molecular Weight:593.785
Hs Code.:

Synonyms:(2R,5R)-5-<4-(benzyloxy)butyl>-N-<(benzyloxy)carbonyl>-2-<4-(p-toluenesulfonyloxy)butyl>pyrrolidine

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Chemical Property of (2R,5R)-5-<4-(benzyloxy)butyl>-N-<(benzyloxy)carbonyl>-2-<4-(p-toluenesulfonyloxy)butyl>pyrrolidine

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Technology Process of (2R,5R)-5-<4-(benzyloxy)butyl>-N-<(benzyloxy)carbonyl>-2-<4-(p-toluenesulfonyloxy)butyl>pyrrolidine

There total 8 articles about (2R,5R)-5-<4-(benzyloxy)butyl>-N-<(benzyloxy)carbonyl>-2-<4-(p-toluenesulfonyloxy)butyl>pyrrolidine 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: 84.0%

: 134822-27-8
(2R,5R)-5-<4-(benzyloxy)butyl>-N-<(benzyloxy)carbonyl>-2-(4-hydroxybutyl)pyrrolidine

: 98-59-9
p-toluenesulfonyl chloride

: 142841-52-9
(2R,5R)-5-<4-(benzyloxy)butyl>-N-<(benzyloxy)carbonyl>-2-<4-(p-toluenesulfonyloxy)butyl>pyrrolidine

Guidance literature:: With dmap; In dichloromethane; for 2h;
DOI:10.1021/jo00045a034

Reference yield:

: 131618-40-1
(5S,8S)-12-(Benzyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>-1-dodecanol

: 142841-52-9
(2R,5R)-5-<4-(benzyloxy)butyl>-N-<(benzyloxy)carbonyl>-2-<4-(p-toluenesulfonyloxy)butyl>pyrrolidine

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / Ambient temperature

2: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

3: thionyl chloride, triethylamine / CH₂Cl₂ / 0.08 h / Ambient temperature

4: RuCl₃*H₂O, NaIO₄ / CCl₄; acetonitrile; H₂O / 1 h / 0 °C

6: 20percent aq. K₂CO₃ / CH₂Cl₂ / 0.25 h / ice bath

7: 97 percent / 1percent methanolic KOH / methanol / 0.5 h / Ambient temperature

8: 84 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h

With dmap; ruthenium trichloride; potassium hydroxide; sodium periodate; thionyl chloride; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; acetonitrile;
DOI:10.1021/jo00045a034

Reference yield:

: 134822-21-2
(5S,8S)-1-(benzoyloxy)-12-(benzyloxy)-5,8-dodecanediol cyclic sulfate

: 142841-52-9
(2R,5R)-5-<4-(benzyloxy)butyl>-N-<(benzyloxy)carbonyl>-2-<4-(p-toluenesulfonyloxy)butyl>pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

2: 20percent aq. K₂CO₃ / CH₂Cl₂ / 0.25 h / ice bath

3: 97 percent / 1percent methanolic KOH / methanol / 0.5 h / Ambient temperature

4: 84 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h

With dmap; potassium hydroxide; potassium carbonate; In methanol; dichloromethane;
DOI:10.1021/jo00045a034