(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ylamine

Base Information

Chemical Name:(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ylamine
CAS No.:216692-27-2
Molecular Formula:C₂₈H₃₆N₂O₃SSi
Molecular Weight:508.757
Hs Code.:

Synonyms:(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ylamine

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Chemical Property of (3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ylamine

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Technology Process of (3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ylamine

There total 7 articles about (3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ylamine 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%

: 216692-17-0
(2S,4S)-4-Azido-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidine

: 216692-27-2
(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ylamine

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethanol; water; ethyl acetate; for 2.5h;
DOI:10.1016/S0040-4020(98)00821-7

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 216692-27-2
(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ylamine

Guidance literature:: Multi-step reaction with 5 steps

1: 84 percent / Et₃N, DMAP / CH₂Cl₂ / 48 h / Ambient temperature

2: LiBH₄ / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 1 h

3: 100 percent / imidazole, DMAP / CH₂Cl₂ / 18 h

4: 87 percent / aq. NaN₃ / dimethylformamide / 1.) 70 deg C, 5 h, 2.) room temperature, 18 h

5: 100 percent / H₂ / Pd/C / ethanol; H₂O; ethyl acetate / 2.5 h

With 1H-imidazole; dmap; lithium borohydride; sodium azide; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(98)00821-7

Reference yield:

: 118329-82-1
(2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

: 216692-27-2
(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ylamine

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / imidazole, DMAP / CH₂Cl₂ / 18 h

2: 87 percent / aq. NaN₃ / dimethylformamide / 1.) 70 deg C, 5 h, 2.) room temperature, 18 h

3: 100 percent / H₂ / Pd/C / ethanol; H₂O; ethyl acetate / 2.5 h

With 1H-imidazole; dmap; sodium azide; hydrogen; palladium on activated charcoal; In ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(98)00821-7