(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-4-acetoxy-2-butyne

Base Information

Chemical Name:(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-4-acetoxy-2-butyne
CAS No.:782496-14-4
Molecular Formula:C₆₁H₈₆N₂O₉Si₃
Molecular Weight:1075.62
Hs Code.:

(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-4-acetoxy-2-butyne

Synonyms:(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-4-acetoxy-2-butyne

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Chemical Property of (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-4-acetoxy-2-butyne

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Technology Process of (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-4-acetoxy-2-butyne

There total 1 articles about (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-4-acetoxy-2-butyne 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%

: 782496-06-4
(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

: 108-24-7
acetic anhydride

: 782496-14-4
(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-4-acetoxy-2-butyne

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h;
DOI:10.1002/chem.200400181

Reference yield: 100.0%

: 782496-14-4
(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-4-acetoxy-2-butyne

: 782496-16-6
(2'S,5'S,2''S,5''S,1R,4S)-1,4-bis-[N'-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-4-acetoxy-2-butyn-1-ol

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

Reference yield:

: 782496-14-4
(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-4-acetoxy-2-butyne

: 782496-22-4
(2S,5S,2'S,5'S,2''S,5''S)-2,5-bis-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-tetrahydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / CSA / tetrahydrofuran; methanol / 0.25 h / -10 °C

2.1: 98 percent / H₂ / Pt/C / ethyl acetate / 16 h / 760 Torr

3.1: 94 percent / NEt₃ / CH₂Cl₂ / -50 - -15 °C

4.1: MeLi / tetrahydrofuran; various solvent(s) / 1 h / -78 - 0 °C

4.2: 44 percent / t-BuOK / tetrahydrofuran; various solvent(s) / 0.5 h / 0 - 20 °C

With camphor-10-sulfonic acid; methyllithium; hydrogen; triethylamine; platinum on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1002/chem.200400181