(2S,4R)-4-(allyloxy)-1-((benzyloxy)carbonyl)pyrrolidine-2-carboxylic acid

Base Information

Chemical Name:(2S,4R)-4-(allyloxy)-1-((benzyloxy)carbonyl)pyrrolidine-2-carboxylic acid
CAS No.:523987-31-7
Molecular Formula:C₁₆H₁₉NO₅
Molecular Weight:305.331
Hs Code.:

Synonyms:(2S,4R)-4-(allyloxy)-1-((benzyloxy)carbonyl)pyrrolidine-2-carboxylic acid

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Chemical Property of (2S,4R)-4-(allyloxy)-1-((benzyloxy)carbonyl)pyrrolidine-2-carboxylic acid

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Technology Process of (2S,4R)-4-(allyloxy)-1-((benzyloxy)carbonyl)pyrrolidine-2-carboxylic acid

There total 5 articles about (2S,4R)-4-(allyloxy)-1-((benzyloxy)carbonyl)pyrrolidine-2-carboxylic acid 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: 100.0%

: 106-95-6
allyl bromide

: 13504-85-3
(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

: 523987-31-7
(2S,4R)-4-(allyloxy)-1-((benzyloxy)carbonyl)pyrrolidine-2-carboxylic acid

Guidance literature:: (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid; With sodium hydride; In tetrahydrofuran; dimethyl sulfoxide; mineral oil; at -20 - 0 ℃; Inert atmosphere;

allyl bromide; In tetrahydrofuran; dimethyl sulfoxide; mineral oil; at -20 - 25 ℃; for 24h; chemoselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201402429

Reference yield: 90.0%

: 523987-30-6
allyl N-benzyloxycarbonyl-trans-4-(allyloxy)-L-prolinate

: 523987-31-7
(2S,4R)-4-(allyloxy)-1-((benzyloxy)carbonyl)pyrrolidine-2-carboxylic acid

Guidance literature:: With sodium hydroxide; In methanol; at 20 ℃; for 24h;
DOI:10.1016/S0957-4166(02)00796-6

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 523987-31-7
(2S,4R)-4-(allyloxy)-1-((benzyloxy)carbonyl)pyrrolidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: 97 percent / aq. NaHCO₃ / tetrahydrofuran / 20 °C

2.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.2: 57 percent / dimethylformamide / 20 °C

3.1: 90 percent / aq. NaOH / methanol / 24 h / 20 °C

With sodium hydroxide; sodium hydride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(02)00796-6