(2R,4S)-2-azidomethyl-4-(p-toluenesulfonyl)oxy-N-(tert-butoxycarbonylmethyl)pyrrolidine

Base Information

Chemical Name:(2R,4S)-2-azidomethyl-4-(p-toluenesulfonyl)oxy-N-(tert-butoxycarbonylmethyl)pyrrolidine
CAS No.:718632-77-0
Molecular Formula:C₁₈H₂₆N₄O₅S
Molecular Weight:410.494
Hs Code.:

Synonyms:(2R,4S)-2-azidomethyl-4-(p-toluenesulfonyl)oxy-N-(tert-butoxycarbonylmethyl)pyrrolidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,4S)-2-azidomethyl-4-(p-toluenesulfonyl)oxy-N-(tert-butoxycarbonylmethyl)pyrrolidine

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Technology Process of (2R,4S)-2-azidomethyl-4-(p-toluenesulfonyl)oxy-N-(tert-butoxycarbonylmethyl)pyrrolidine

There total 9 articles about (2R,4S)-2-azidomethyl-4-(p-toluenesulfonyl)oxy-N-(tert-butoxycarbonylmethyl)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: 86.0%

: 98-59-9
p-toluenesulfonyl chloride

: 718632-76-9
(2R,4S)-2-azidomethyl-4-hydroxy-N-(tert-butoxycarbonylmethyl)-pyrrolidine

: 718632-77-0
(2R,4S)-2-azidomethyl-4-(p-toluenesulfonyl)oxy-N-(tert-butoxycarbonylmethyl)pyrrolidine

Guidance literature:: With pyridine; for 18h;
DOI:10.1039/b315768g

Reference yield: 66.0%

: 80-48-8
methyl p-toluene sulfonate

: 718632-74-7
(2R,4R)-2-azidomethyl-4-hydroxy-N-(tert-butoxycarbonylmethyl)-pyrrolidine

: 718632-77-0
(2R,4S)-2-azidomethyl-4-(p-toluenesulfonyl)oxy-N-(tert-butoxycarbonylmethyl)pyrrolidine

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -10 - 20 ℃; for 18h;
DOI:10.1039/b315768g

Reference yield:

: 114676-58-3
(2R,4R)-tert-butyl 4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

: 718632-77-0
(2R,4S)-2-azidomethyl-4-(p-toluenesulfonyl)oxy-N-(tert-butoxycarbonylmethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1: 99 percent / diisopropylethylamine / CH₂Cl₂ / 0.25 h / 0 °C

2: 57 percent / NaN₃ / dimethylformamide / 16 h / 80 °C

3: 99 percent / HCl / dioxane; CH₂Cl₂ / 2.25 h / 0 - 20 °C

4: 94 percent / diisopropylethyl amine / CH₂Cl₂ / 24 h / 0 - 20 °C

5: 80 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 18 h / -30 - 20 °C

6: 92 percent / aq. NH₃ / methanol / 2 h

7: 86 percent / pyridine / 18 h

With pyridine; hydrogenchloride; ammonium hydroxide; sodium azide; di-isopropyl azodicarboxylate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; 5: Mitsunobu reaction;
DOI:10.1039/b315768g