(2S,5S,2'S,5'S,2''S,5''S)-2,5-bis-[N'-tert-butoxycarbonyl-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-[N'-tert-butoxycarbonyl-5'-(tert-butyldiphenylsilyloxy)methyl]-pyrrolidin-2'-yl-tetrahydrofuran
CAS No.:782496-22-4
Molecular Formula:C₅₆H₇₈N₂O₇Si₂
Molecular Weight:947.416
Hs Code.:

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

There total 4 articles about (2S,5S,2'S,5'S,2''S,5''S)-2,5-bis-[N'-tert-butoxycarbonyl-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: 44.0%

: C₅₉H₈₄N₂O₁₁SSi₂

: (1,2-bis-[8'-(tert-butyldiphenylsilyloxy)methyl]-1'-aza-3'-oxa-bicyclo[3.3.0]octan-2'-on-4'-yl)-ethane

: 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:: C₅₉H₈₄N₂O₁₁SSi₂; With methyllithium; In tetrahydrofuran; at -78 - 0 ℃; for 1h;

With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h;
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

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

: 782496-22-4
(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 3 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

With methyllithium; hydrogen; triethylamine; platinum on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1002/chem.200400181