(2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine

Base Information

Chemical Name:(2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine
CAS No.:115890-52-3
Molecular Formula:C₁₈H₂₅NO₄
Molecular Weight:319.401
Hs Code.:

Synonyms:(2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine

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Chemical Property of (2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine

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Technology Process of (2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine

There total 15 articles about (2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine 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: 75.0%

: 115890-53-4
1-(benzyloxycarbonyl)kainic acid dimethyl ester

: 115890-52-3
(2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1021/ja00227a029

Reference yield:

: 115890-38-5
((R)-2-Benzyloxy-1-formyl-ethyl)-(3-methyl-but-2-enyl)-carbamic acid benzyl ester

: 115890-52-3
(2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine

Guidance literature:: Multi-step reaction with 8 steps

1: 4.24 g / ethylenediammonium diacetate / propan-2-ol / 16 h / Ambient temperature

2: 2.27 g / H₂O / dioxane / 15 h / Heating

3: 41 percent / BBr₃ / CH₂Cl₂ / 1.) -40 deg C to 0 deg C, 1 h, 2.) 0 deg C, 30 min

4: 83 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 25 h / Ambient temperature

5: 97 percent / NaBH₄ / propan-2-ol / 0.67 h / Heating

6: 85 percent / 2 h / 270 °C

7: 51 mg / K₂CO₃, methanol / 1 h / Ambient temperature

8: 35.8 mg / 1 N n-Bu₄NF / tetrahydrofuran / 0.67 h / Ambient temperature

With methanol; dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; water; boron tribromide; potassium carbonate; ethylenediamine diacetic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; isopropyl alcohol;
DOI:10.1021/ja00227a029

Reference yield:

: (2R,3RS)-2-<(benzyloxycarbonyl)prenylamino>-1-(benzyloxy)-3,4-butandiol

: 115890-52-3
(2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine

Guidance literature:: Multi-step reaction with 9 steps

1: 3.27 g / NaIO₄ / methanol; H₂O / 2 h / 0 °C

2: 4.24 g / ethylenediammonium diacetate / propan-2-ol / 16 h / Ambient temperature

3: 2.27 g / H₂O / dioxane / 15 h / Heating

4: 41 percent / BBr₃ / CH₂Cl₂ / 1.) -40 deg C to 0 deg C, 1 h, 2.) 0 deg C, 30 min

5: 83 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 25 h / Ambient temperature

6: 97 percent / NaBH₄ / propan-2-ol / 0.67 h / Heating

7: 85 percent / 2 h / 270 °C

8: 51 mg / K₂CO₃, methanol / 1 h / Ambient temperature

9: 35.8 mg / 1 N n-Bu₄NF / tetrahydrofuran / 0.67 h / Ambient temperature

With methanol; dmap; sodium tetrahydroborate; sodium periodate; tetrabutyl ammonium fluoride; water; boron tribromide; potassium carbonate; ethylenediamine diacetic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; isopropyl alcohol;
DOI:10.1021/ja00227a029