(2S,5S,1'R,4'R,5'S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[N'-benzyl-5'-(p-tolylsulfonyl)amino-1',4'-dihydroxy]-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-1',4'-dihydroxy]-2'-hexynyl-pyrrolidine
CAS No.:782496-38-2
Molecular Formula:C₄₆H₅₈N₂O₇SSi
Molecular Weight:811.127
Hs Code.:

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

There total 12 articles about (2S,5S,1'R,4'R,5'S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[N'-benzyl-5'-(p-tolylsulfonyl)amino-1',4'-dihydroxy]-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: 95.0%

: 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

: 782496-38-2
(2S,5S,1'R,4'R,5'S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[N'-benzyl-5'-(p-tolylsulfonyl)amino-1',4'-dihydroxy]-2'-hexynyl-pyrrolidine

Guidance literature:: With camphor-10-sulfonic acid; In tetrahydrofuran; methanol; at 0 ℃; for 0.5h;
DOI:10.1002/chem.200400181

Reference yield:

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

: 782496-38-2
(2S,5S,1'R,4'R,5'S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[N'-benzyl-5'-(p-tolylsulfonyl)amino-1',4'-dihydroxy]-2'-hexynyl-pyrrolidine

Guidance literature:: Multi-step reaction with 7 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

7.1: 95 percent / CSA / tetrahydrofuran; methanol / 0.5 h / 0 °C

With 1H-imidazole; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; 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

: 782496-38-2
(2S,5S,1'R,4'R,5'S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[N'-benzyl-5'-(p-tolylsulfonyl)amino-1',4'-dihydroxy]-2'-hexynyl-pyrrolidine

Guidance literature:: Multi-step reaction with 4 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

4.1: 95 percent / CSA / tetrahydrofuran; methanol / 0.5 h / 0 °C

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; 2.1: Swern oxidation;
DOI:10.1002/chem.200400181