(2S,3S,4S)-tert-butyl 3-formyl-1-tosyl-4-vinylpyrrolidine-2-carboxylate

Base Information

Chemical Name:(2S,3S,4S)-tert-butyl 3-formyl-1-tosyl-4-vinylpyrrolidine-2-carboxylate
CAS No.:1508298-36-9
Molecular Formula:C₁₉H₂₅NO₅S
Molecular Weight:379.477
Hs Code.:

Synonyms:(2S,3S,4S)-tert-butyl 3-formyl-1-tosyl-4-vinylpyrrolidine-2-carboxylate

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Chemical Property of (2S,3S,4S)-tert-butyl 3-formyl-1-tosyl-4-vinylpyrrolidine-2-carboxylate

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Technology Process of (2S,3S,4S)-tert-butyl 3-formyl-1-tosyl-4-vinylpyrrolidine-2-carboxylate

There total 7 articles about (2S,3S,4S)-tert-butyl 3-formyl-1-tosyl-4-vinylpyrrolidine-2-carboxylate 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:

: 1508298-37-0
(S,E)-tert-butyl 2-(N-(4-bromobut-2-enyl)-4-methylphenylsulfonamido)-4-oxobutanoate

: 1508298-36-9
(2S,3S,4S)-tert-butyl 3-formyl-1-tosyl-4-vinylpyrrolidine-2-carboxylate

: (2S,3S,4R)-tert-butyl 3-formyl-1-tosyl-4-vinylpyrrolidine-2-carboxylate

: (2S,3R,4R)-tert-butyl 3-formyl-1-tosyl-4-vinylpyrrolidine-2-carboxylate

Guidance literature:: With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In tetrahydrofuran; at 20 ℃; for 1.5h; Overall yield = 71 %; Overall yield = 84.2 mg; stereoselective reaction; Inert atmosphere;
DOI:10.1021/ol4028557

Reference yield:

: 1508298-41-6
(S,E)-tert-butyl 2-(N-(4-bromobut-2-enyl)-4-methylphenylsulfonamido)-4,4-dimethoxybutanoate

: 1508298-36-9
(2S,3S,4S)-tert-butyl 3-formyl-1-tosyl-4-vinylpyrrolidine-2-carboxylate

: (2S,3S,4R)-tert-butyl 3-formyl-1-tosyl-4-vinylpyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: pyridinium p-toluenesulfonate / water; acetone / 27 h / 60 °C / Inert atmosphere

2: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; pyrrolidine / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; water; acetone; 2: |Tsuji-Trost Allylation;
DOI:10.1021/ol4028557

Reference yield:

: 81477-94-3
N-(diphenylmethylene)glycine tert-butyl ester

: 1508298-36-9
(2S,3S,4S)-tert-butyl 3-formyl-1-tosyl-4-vinylpyrrolidine-2-carboxylate

: (2S,3S,4R)-tert-butyl 3-formyl-1-tosyl-4-vinylpyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: N-(9-anthracenylmethyl)-cinchonidinium chloride; potassium hydroxide / water; toluene / 18 h / 20 °C / Darkness

1.2: 3 h / 20 °C

2.1: triethylamine; dmap / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

3.1: ozone / dichloromethane; methanol / 0.5 h / -78 °C

3.2: 18 h / -78 - 20 °C

4.1: cerium(III) chloride heptahydrate / methanol / 168 h / 20 °C / Inert atmosphere

5.1: sodium hydride / dimethyl sulfoxide / 0.25 h / 20 °C / Inert atmosphere

5.2: 1 h / 20 °C / Inert atmosphere

6.1: pyridinium p-toluenesulfonate / water; acetone / 27 h / 60 °C / Inert atmosphere

7.1: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; pyrrolidine / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

With pyrrolidine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cerium(III) chloride heptahydrate; pyridinium p-toluenesulfonate; sodium hydride; ozone; triethylamine; N-(9-anthracenylmethyl)-cinchonidinium chloride; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; acetone; toluene; 7.1: |Tsuji-Trost Allylation;
DOI:10.1021/ol4028557