(3S,5S)-1,5-bis[(tert-butoxy)carbonyl]-3-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)pyrrolidine-3-carboxylic acid

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Chemical Name:(3S,5S)-1,5-bis[(tert-butoxy)carbonyl]-3-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)pyrrolidine-3-carboxylic acid
CAS No.:1407162-62-2
Molecular Formula:C₂₇H₃₈N₂O₉
Molecular Weight:534.607
Hs Code.:

Synonyms:(3S,5S)-1,5-bis[(tert-butoxy)carbonyl]-3-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)pyrrolidine-3-carboxylic acid

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Chemical Property of (3S,5S)-1,5-bis[(tert-butoxy)carbonyl]-3-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)pyrrolidine-3-carboxylic acid

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Technology Process of (3S,5S)-1,5-bis[(tert-butoxy)carbonyl]-3-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)pyrrolidine-3-carboxylic acid

There total 6 articles about (3S,5S)-1,5-bis[(tert-butoxy)carbonyl]-3-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)pyrrolidine-3-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: 75.0%

: 1407162-55-3
(3S,5S)-3-amino-1,5-bis(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

: 1407162-52-0
2-formylbenzyl allyl chloroformate

: 1407162-62-2
(3S,5S)-1,5-bis[(tert-butoxy)carbonyl]-3-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)pyrrolidine-3-carboxylic acid

Guidance literature:: (3S,5S)-3-amino-1,5-bis(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid; 2-formylbenzyl allyl chloroformate; In methanol; at 20 ℃; for 0.5h;

With sodium cyanoborohydride; In methanol; at 20 ℃; for 12h;
DOI:10.1021/ja3069648

Reference yield:

: 526222-96-8
(5S,8S)-2,4-dioxo-1,3,7-triazaspiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester

: 1407162-62-2
(3S,5S)-1,5-bis[(tert-butoxy)carbonyl]-3-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)pyrrolidine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: hydrogen; palladium on activated charcoal / tetrahydrofuran / 20 °C

2.1: di-tert-butyl dicarbonate; dmap / tetrahydrofuran / 1.5 h / 20 °C

2.2: 0.5 h / 20 °C

3.1: methanol / 0.5 h / 20 °C

3.2: 12 h / 20 °C

With dmap; di-tert-butyl dicarbonate; palladium on activated charcoal; hydrogen; In tetrahydrofuran; methanol;
DOI:10.1021/ja3069648

Reference yield:

: 265670-84-6
7,8-di-tert-butyl (5S,8S)-2,4-dioxo-1,3,7-triazaspiro[4,4]nonane-7,8-dicarboxylate

: 1407162-62-2
(3S,5S)-1,5-bis[(tert-butoxy)carbonyl]-3-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)pyrrolidine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: di-tert-butyl dicarbonate; dmap / tetrahydrofuran / 1.5 h / 20 °C

1.2: 0.5 h / 20 °C

2.1: methanol / 0.5 h / 20 °C

2.2: 12 h / 20 °C

With dmap; di-tert-butyl dicarbonate; In tetrahydrofuran; methanol;
DOI:10.1021/ja3069648