(2S,5S,2'S,5'S,2''S,5''S)-2,5-bis-[5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-tetrahydrofuran

Base Information

Chemical Name:(2S,5S,2'S,5'S,2''S,5''S)-2,5-bis-[5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-tetrahydrofuran
CAS No.:782496-26-8
Molecular Formula:C₄₆H₆₂N₂O₃Si₂
Molecular Weight:747.181
Hs Code.:

Synonyms:(2S,5S,2'S,5'S,2''S,5''S)-2,5-bis-[5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-tetrahydrofuran

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Chemical Property of (2S,5S,2'S,5'S,2''S,5''S)-2,5-bis-[5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-tetrahydrofuran

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Technology Process of (2S,5S,2'S,5'S,2''S,5''S)-2,5-bis-[5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-tetrahydrofuran

There total 5 articles about (2S,5S,2'S,5'S,2''S,5''S)-2,5-bis-[5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-tetrahydrofuran 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: 98.0%

: 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

: 782496-26-8
(2S,5S,2'S,5'S,2''S,5''S)-2,5-bis-[5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-tetrahydrofuran

Guidance literature:: (2S,5S,2'S,5'S,2''S,5''S)-2,5-bis-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-tetrahydrofuran; With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether; In dichloromethane; at -78 - 20 ℃;

With sodium phosphate; In dichloromethane; pH=12;
DOI:10.1002/chem.200400181

Reference yield:

: 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

: 782496-26-8
(2S,5S,2'S,5'S,2''S,5''S)-2,5-bis-[5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-tetrahydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1.1: 98 percent / H₂ / Pt/C / ethyl acetate / 16 h / 760 Torr

2.1: 94 percent / NEt₃ / CH₂Cl₂ / -50 - -15 °C

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

3.2: 44 percent / t-BuOK / tetrahydrofuran; various solvent(s) / 0.5 h / 0 - 20 °C

4.1: thioanisole; 2,6-lutidine; TMSOTf / CH₂Cl₂ / -78 - 20 °C

4.2: 98 percent / aq. Na₃PO₄ / CH₂Cl₂ / pH 12

With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether; methyllithium; hydrogen; triethylamine; platinum on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;
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

: 782496-26-8
(2S,5S,2'S,5'S,2''S,5''S)-2,5-bis-[5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-tetrahydrofuran

Guidance literature:: Multi-step reaction with 5 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

5.1: thioanisole; 2,6-lutidine; TMSOTf / CH₂Cl₂ / -78 - 20 °C

5.2: 98 percent / aq. Na₃PO₄ / CH₂Cl₂ / pH 12

With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether; camphor-10-sulfonic acid; methyllithium; hydrogen; triethylamine; platinum on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1002/chem.200400181