(2'S,5'S,2''S,5''S,1R,4R)-1,4-bis-[N'-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-1-(trimethylsilyl)oxy-2-butyn-4-ol

Base Information

Chemical Name:(2'S,5'S,2''S,5''S,1R,4R)-1,4-bis-[N'-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-1-(trimethylsilyl)oxy-2-butyn-4-ol
CAS No.:782496-05-3
Molecular Formula:C₅₉H₈₄N₂O₈Si₃
Molecular Weight:1033.58
Hs Code.:

Synonyms:(2'S,5'S,2''S,5''S,1R,4R)-1,4-bis-[N'-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-1-(trimethylsilyl)oxy-2-butyn-4-ol

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Chemical Property of (2'S,5'S,2''S,5''S,1R,4R)-1,4-bis-[N'-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-1-(trimethylsilyl)oxy-2-butyn-4-ol

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Technology Process of (2'S,5'S,2''S,5''S,1R,4R)-1,4-bis-[N'-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-1-(trimethylsilyl)oxy-2-butyn-4-ol

There total 8 articles about (2'S,5'S,2''S,5''S,1R,4R)-1,4-bis-[N'-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-1-(trimethylsilyl)oxy-2-butyn-4-ol 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: 91.0%

: 192389-28-9
(2S,5S)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)-methyl-pyrrolidine-5-carbaldehyde

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

: 782496-05-3
(2'S,5'S,2''S,5''S,1R,4R)-1,4-bis-[N'-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-1-(trimethylsilyl)oxy-2-butyn-4-ol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -90 ℃; for 1h;
DOI:10.1016/S0040-4039(97)00845-9

Reference yield: 54.0%

: 192389-28-9
(2S,5S)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)-methyl-pyrrolidine-5-carbaldehyde

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

: 782496-06-4
(2'S,5'S,2''S,5''S,1R,4S)-1,4-bis-[N'-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-1-(trimethylsilyl)oxy-2-butyn-4-ol

: 782496-05-3
(2'S,5'S,2''S,5''S,1R,4R)-1,4-bis-[N'-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-1-(trimethylsilyl)oxy-2-butyn-4-ol

Guidance literature:: (2S,5S,1'R)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-[1'-(trimethylsilyl)oxy]-prop-2'-ynyl-pyrrolidine; With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; hexane; at -80 ℃; for 0.75h;

(2S,5S)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)-methyl-pyrrolidine-5-carbaldehyde; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -80 - -70 ℃; for 1.5h;
DOI:10.1002/chem.200400181

Reference yield:

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

: 782496-05-3
(2'S,5'S,2''S,5''S,1R,4R)-1,4-bis-[N'-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-1-(trimethylsilyl)oxy-2-butyn-4-ol

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; HMPT / tetrahydrofuran; hexane / 0.75 h / -80 °C

6.2: 54 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1.5 h / -80 - -70 °C

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