(2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine

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Chemical Name:(2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine
CAS No.:782496-46-2
Molecular Formula:C₄₆H₆₁N₃O₅SSi
Molecular Weight:796.159
Hs Code.:

Synonyms:(2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine

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Chemical Property of (2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine

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Technology Process of (2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine

There total 2 articles about (2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[1''-(N''-benzyl-N''-tosyl)amino]-ethyl-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:

: 782496-42-8
(2S/R,4R,7R,2'S,5'S,1''S)-4-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-7-[1''-N''-benzyl-(p-tolylsulfonyl)amino]-ethyl-2,2-dioxo-1,3-dioxathiepane

: 782496-46-2
(2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine

Guidance literature:: (2S/R,4R,7R,2'S,5'S,1''S)-4-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-7-[1''-N''-benzyl-(p-tolylsulfonyl)amino]-ethyl-2,2-dioxo-1,3-dioxathiepane; With tetrabutylammoniun azide; In tetrahydrofuran; at 35 ℃; for 36h;

With sulfuric acid; In tetrahydrofuran; for 8h; pH=1 - 2;

With methanesulfonyl chloride; triethylamine; In dichloromethane; at -40 - -15 ℃; for 1h;
DOI:10.1002/chem.200400181

Reference yield:

: (2S/R,4R,7R,2'S,5'S,1''S)-4-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-7-[1''-N''-benzyl-(p-tolylsulfonyl)amino]-ethyl-2-oxo-1,3-dioxathiepane

: 782496-46-2
(2S,5S,2'S,5'S,1''S)-2-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-5-[1''-(N''-benzyl-N''-tosyl)amino]-ethyl-pyrrolidine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 98 percent / aq. NaIO₄ / RuCl₃ / CCl₄; acetonitrile / 0.33 h / 0 °C

2.1: tetrabutylammonium azide / tetrahydrofuran / 36 h / 35 °C

2.2: H₂SO₄ / tetrahydrofuran / 8 h / pH 1 - 2

2.3: 330 mg / MsCl; Et₃N / CH₂Cl₂ / 1 h / -40 - -15 °C

With sodium periodate; tetrabutylammoniun azide; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; acetonitrile;
DOI:10.1002/chem.200400181