(2S,5S,1'R,4'R,5'S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[N'-benzyl-5'-(p-tolylsulfonyl)amino-4'-hydroxy-1'-(trimethylsilyl)oxy]-2'-hexynyl-pyrrolidine

Base Information

Chemical Name:(2S,5S,1'R,4'R,5'S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[N'-benzyl-5'-(p-tolylsulfonyl)amino-4'-hydroxy-1'-(trimethylsilyl)oxy]-2'-hexynyl-pyrrolidine
CAS No.:782496-36-0
Molecular Formula:C₄₉H₆₆N₂O₇SSi₂
Molecular Weight:883.309
Hs Code.:

(2S,5S,1'R,4'R,5'S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[N'-benzyl-5'-(p-tolylsulfonyl)amino-4'-hydroxy-1'-(trimethylsilyl)oxy]-2'-hexynyl-pyrrolidine

Synonyms:(2S,5S,1'R,4'R,5'S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[N'-benzyl-5'-(p-tolylsulfonyl)amino-4'-hydroxy-1'-(trimethylsilyl)oxy]-2'-hexynyl-pyrrolidine

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Chemical Property of (2S,5S,1'R,4'R,5'S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[N'-benzyl-5'-(p-tolylsulfonyl)amino-4'-hydroxy-1'-(trimethylsilyl)oxy]-2'-hexynyl-pyrrolidine

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Technology Process of (2S,5S,1'R,4'R,5'S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[N'-benzyl-5'-(p-tolylsulfonyl)amino-4'-hydroxy-1'-(trimethylsilyl)oxy]-2'-hexynyl-pyrrolidine

There total 10 articles about (2S,5S,1'R,4'R,5'S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[N'-benzyl-5'-(p-tolylsulfonyl)amino-4'-hydroxy-1'-(trimethylsilyl)oxy]-2'-hexynyl-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: 92.0%

: 192389-34-7
(2S,5S,1'R)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[1'-(trimethylsilyl)oxy]-prop-2'-ynyl-pyrrolidine

: 197247-27-1
N-benzyl-4-methyl-N-(1-oxopropan-2-yl)benzenesulfonamide

: 782496-36-0
(2S,5S,1'R,4'R,5'S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[N'-benzyl-5'-(p-tolylsulfonyl)amino-4'-hydroxy-1'-(trimethylsilyl)oxy]-2'-hexynyl-pyrrolidine

Guidance literature:: (2S,5S,1'R)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[1'-(trimethylsilyl)oxy]-prop-2'-ynyl-pyrrolidine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.666667h;

N-benzyl-4-methyl-N-(1-oxopropan-2-yl)benzenesulfonamide; In tetrahydrofuran; hexane; at -78 - -25 ℃; for 3.5h;
DOI:10.1002/chem.200400181

Reference yield:

: 192389-29-0
(2S,5S/R)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)methyl-5-methoxy-pyrrolidine

: 782496-36-0
(2S,5S,1'R,4'R,5'S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[N'-benzyl-5'-(p-tolylsulfonyl)amino-4'-hydroxy-1'-(trimethylsilyl)oxy]-2'-hexynyl-pyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 72 percent / TMSOTf / CH₂Cl₂ / 0.05 h / -35 °C

2.1: 66 percent / DIBAH / toluene; petroleum ether; hexane / 1 h / -60 °C

3.1: tetrahydrofuran / 4 h / -40 - 0 °C

4.1: 97 percent / aq. K₂CO₃ / tetrahydrofuran; methanol / 4 h

5.1: 97 percent / imidazole / CH₂Cl₂ / 0.5 h / 0 °C

6.1: nBuLi / tetrahydrofuran; hexane / 0.67 h / -78 °C

6.2: 92 percent / tetrahydrofuran; hexane / 3.5 h / -78 - -25 °C

With 1H-imidazole; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; Petroleum ether;
DOI:10.1002/chem.200400181

Reference yield:

: (S)-2-[Benzyl-(toluene-4-sulfonyl)-amino]-propionic acid benzyl ester

: 782496-36-0
(2S,5S,1'R,4'R,5'S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[N'-benzyl-5'-(p-tolylsulfonyl)amino-4'-hydroxy-1'-(trimethylsilyl)oxy]-2'-hexynyl-pyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1.1: 7.88 g / LiAlH₄ / tetrahydrofuran / 1 h

2.1: 77 percent / DMSO; (COCl)2; EtN(iPr)2 / CH₂Cl₂ / 0.83 h / -80 - 0 °C

3.1: nBuLi / tetrahydrofuran; hexane / 0.67 h / -78 °C

3.2: 92 percent / tetrahydrofuran; hexane / 3.5 h / -78 - -25 °C

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 2.1: Swern oxidation;
DOI:10.1002/chem.200400181