(2S,3S,4S)-3-(2-acetoxyethyl)-1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-isopropenylpyrrolidine

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Chemical Name:(2S,3S,4S)-3-(2-acetoxyethyl)-1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-isopropenylpyrrolidine
CAS No.:115890-50-1
Molecular Formula:C₂₆H₄₁NO₅Si
Molecular Weight:475.701
Hs Code.:

Synonyms:(2S,3S,4S)-3-(2-acetoxyethyl)-1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-isopropenylpyrrolidine

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Chemical Property of (2S,3S,4S)-3-(2-acetoxyethyl)-1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-isopropenylpyrrolidine

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Technology Process of (2S,3S,4S)-3-(2-acetoxyethyl)-1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-isopropenylpyrrolidine

There total 10 articles about (2S,3S,4S)-3-(2-acetoxyethyl)-1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-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: 85.0%

: 108-24-7
acetic anhydride

: 115890-49-8
(2S,3S,4R)-1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-3-(2-hydroxyethyl)-4-(1-hydroxy-1-methylethyl)pyrrolidine

: 115890-50-1
(2S,3S,4S)-3-(2-acetoxyethyl)-1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-isopropenylpyrrolidine

Guidance literature:: at 270 ℃; for 2h;
DOI:10.1021/ja00227a029

Reference yield:

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

: 115890-50-1
(2S,3S,4S)-3-(2-acetoxyethyl)-1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-isopropenylpyrrolidine

Guidance literature:: Multi-step reaction with 6 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

With dmap; sodium tetrahydroborate; water; boron tribromide; ethylenediamine diacetic acid; triethylamine; In 1,4-dioxane; dichloromethane; isopropyl alcohol;
DOI:10.1021/ja00227a029

Reference yield:

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

: 115890-50-1
(2S,3S,4S)-3-(2-acetoxyethyl)-1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-4-isopropenylpyrrolidine

Guidance literature:: Multi-step reaction with 7 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

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