(2'S,5'S,2''S,5''S,1R,4R)-1,4-bis-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-2-butyne-1,4-diol

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-2-butyne-1,4-diol
CAS No.:192389-27-8
Molecular Formula:C₅₆H₇₆N₂O₈Si₂
Molecular Weight:961.399
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-2-butyne-1,4-diol

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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-2-butyne-1,4-diol

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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-2-butyne-1,4-diol

There total 7 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-2-butyne-1,4-diol 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: 94.0%

: 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

: 192389-27-8
(2'S,5'S,2''S,5''S,1R,4R)-1,4-bis-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-2-butyne-1,4-diol

Guidance literature:: With camphor-10-sulfonic acid; In tetrahydrofuran; methanol; at -10 ℃; for 0.25h;
DOI:10.1002/chem.200400181

Reference yield:

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

: 192389-27-8
(2'S,5'S,2''S,5''S,1R,4R)-1,4-bis-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-2-butyne-1,4-diol

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

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

7.1: 94 percent / CSA / tetrahydrofuran; methanol / 0.25 h / -10 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; 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:

: 192389-32-5
(2S,5S,1'R)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-(1'-hydroxy-3'-trimethylsilyl)-prop-2'-ynyl-pyrrolidine

: 192389-27-8
(2'S,5'S,2''S,5''S,1R,4R)-1,4-bis-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-2-butyne-1,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / aq. K₂CO₃ / tetrahydrofuran; methanol / 4 h

2.1: 97 percent / imidazole / CH₂Cl₂ / 0.5 h / 0 °C

3.1: nBuLi; HMPT / tetrahydrofuran; hexane / 0.75 h / -80 °C

3.2: 54 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1.5 h / -80 - -70 °C

4.1: 94 percent / CSA / tetrahydrofuran; methanol / 0.25 h / -10 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; camphor-10-sulfonic acid; potassium carbonate; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1002/chem.200400181