(2R,3S,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1R)-1-hydroxy-3-butenyl>pyrrolidine

Base Information

Chemical Name:(2R,3S,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1R)-1-hydroxy-3-butenyl>pyrrolidine
CAS No.:113626-58-7
Molecular Formula:C₂₉H₃₃NO₃
Molecular Weight:443.586
Hs Code.:

Synonyms:(2R,3S,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1R)-1-hydroxy-3-butenyl>pyrrolidine

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Chemical Property of (2R,3S,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1R)-1-hydroxy-3-butenyl>pyrrolidine

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Technology Process of (2R,3S,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1R)-1-hydroxy-3-butenyl>pyrrolidine

There total 31 articles about (2R,3S,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1R)-1-hydroxy-3-butenyl>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: 22.0%

: 2622-05-1
allylmagnesium bromide

: 132430-65-0
(2S,3S,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidine-2-carbaldehyde

: 113626-58-7
(2R,3S,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1R)-1-hydroxy-3-butenyl>pyrrolidine

: 113626-61-2
(2R,3S,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1S)-1-hydroxy-3-butenyl>pyrrolidine

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1248/cpb.38.2712

Reference yield:

: 101758-68-3
(R)-(+)-5-triphenylmethyloxymethyl-2 (5H)-furanone

: 113626-58-7
(2R,3S,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1R)-1-hydroxy-3-butenyl>pyrrolidine

Guidance literature:: Multi-step reaction with 11 steps

1: 52 percent / OsO₄, N-methylmorpholine N-oxide / H₂O; acetone

2: p-TsOH / acetone

3: 1.) LiAlH₄; 2.) pyridine; 3.) NaN₃ / 1.) THF; 3.) DMF, 130 deg C

4: 65 percent / H₂ / Pd black / ethanol

5: K₂CO₃ / ethanol

6: cc. HCl / methanol

7: N,N-diethylaniline

8: 10 percent HCl / methanol / 40 °C

9: NaH / tetrahydrofuran; dimethylformamide

10: 10 percent HCl / methanol / 70 °C

11: 2.) copper(I) iodide / 2.) THF, dimethylsulfide

With pyridine; hydrogenchloride; copper(l) iodide; lithium aluminium tetrahydride; sodium azide; hydrogen; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; N,N-diethylaniline; osmium(VIII) oxide; palladium; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1248/cpb.35.2140

Reference yield:

: 113571-61-2
(S)-1-benzyl-5-benzyloxymethyl-2-oxo-3-pyrroline

: 113626-58-7
(2R,3S,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1R)-1-hydroxy-3-butenyl>pyrrolidine

Guidance literature:: Multi-step reaction with 9 steps

1: OsO₄

2: p-TsOH / acetone

3: H₂ / Pd black / methanol

4: borane, dimethylsulfide / tetrahydrofuran

5: N,N-diethylaniline

6: 10 percent HCl / methanol / 40 °C

7: NaH / tetrahydrofuran; dimethylformamide

8: 10 percent HCl / methanol / 70 °C

9: 2.) copper(I) iodide / 2.) THF, dimethylsulfide

With hydrogenchloride; copper(l) iodide; dimethylsulfide; borane; hydrogen; sodium hydride; toluene-4-sulfonic acid; N,N-diethylaniline; osmium(VIII) oxide; palladium; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetone;
DOI:10.1248/cpb.35.2140