(2R,3S,4S)-3-Acetoxy-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)pyrrolidine

Base Information

Chemical Name:(2R,3S,4S)-3-Acetoxy-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)pyrrolidine
CAS No.:180081-83-8
Molecular Formula:C₂₅H₄₁NO₆Si
Molecular Weight:479.689
Hs Code.:

Synonyms:(2R,3S,4S)-3-Acetoxy-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)pyrrolidine

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Chemical Property of (2R,3S,4S)-3-Acetoxy-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)pyrrolidine

Chemical Property:

Purity/Quality:

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Hazard Codes:

MSDS Files:: SDS file from LookChem

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Technology Process of (2R,3S,4S)-3-Acetoxy-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)pyrrolidine

There total 17 articles about (2R,3S,4S)-3-Acetoxy-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)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: 94.0%

: 108-24-7
acetic anhydride

: 249617-08-1
(2R,3S,4S)-1-(tert-Butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-2-(4-methoxybenzyl)pyrrolidine

: 180081-83-8
(2R,3S,4S)-3-Acetoxy-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)pyrrolidine

Guidance literature:: With pyridine; dmap; at 20 ℃; for 3h;
DOI:10.1055/s-1999-3661

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 180081-83-8
(2R,3S,4S)-3-Acetoxy-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / imidazole / dimethylformamide / 17 h / 50 °C

2: H₂ / 10 percent Pd(OH)2/C / dioxane / 72 h / 20 °C / 3000.24 Torr

3: H₂ / 10 percent Pd(OH)2/C / dioxane; acetic acid / 24 h / 20 °C

4: 94 percent / pyridine; DMAP / 3 h / 20 °C

With pyridine; 1H-imidazole; dmap; hydrogen; palladium dihydroxide; In 1,4-dioxane; acetic acid; N,N-dimethyl-formamide; 1: Etherification / 2: Catalytic hydrogenation / 3: Hydrogenolysis / 4: Acetylation;
DOI:10.1055/s-1999-3661

Reference yield:

: 186465-19-0
(2S,3S)-N,2-O-Dibenzyl-3,4-O-isopropylidene-L-threose imine

: 180081-83-8
(2R,3S,4S)-3-Acetoxy-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1.1: Mg; I₂ / diethyl ether / 0.25 h / Heating

1.2: diethyl ether / 3 h / 20 °C

2.1: H₂O; HCl / dioxane / 20 °C

3.1: 77 percent / DEAD; PPh₃; pyridine / 1.5 h / 0 °C

4.1: 98 percent / imidazole / dimethylformamide / 17 h / 50 °C

5.1: H₂ / 10 percent Pd(OH)2/C / dioxane / 72 h / 20 °C / 3000.24 Torr

6.1: H₂ / 10 percent Pd(OH)2/C / dioxane; acetic acid / 24 h / 20 °C

7.1: 94 percent / pyridine; DMAP / 3 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; water; hydrogen; iodine; magnesium; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; In 1,4-dioxane; diethyl ether; acetic acid; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Grignard reaction / 2.1: Hydrolysis / 3.1: Cyclization / 4.1: Etherification / 5.1: Catalytic hydrogenation / 6.1: Hydrogenolysis / 7.1: Acetylation;
DOI:10.1055/s-1999-3661