1,1'-di-tert-butoxycarbonyl-5,5'-bis(tert-butyldiphenylsilanyloxymethyl)-2,3'-bipyrrolidine

Base Information

Chemical Name:1,1'-di-tert-butoxycarbonyl-5,5'-bis(tert-butyldiphenylsilanyloxymethyl)-2,3'-bipyrrolidine
CAS No.:930769-33-8
Molecular Formula:C₅₂H₇₂N₂O₆Si₂
Molecular Weight:877.324
Hs Code.:

Synonyms:1,1'-di-tert-butoxycarbonyl-5,5'-bis(tert-butyldiphenylsilanyloxymethyl)-2,3'-bipyrrolidine

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Chemical Property of 1,1'-di-tert-butoxycarbonyl-5,5'-bis(tert-butyldiphenylsilanyloxymethyl)-2,3'-bipyrrolidine

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Technology Process of 1,1'-di-tert-butoxycarbonyl-5,5'-bis(tert-butyldiphenylsilanyloxymethyl)-2,3'-bipyrrolidine

There total 7 articles about 1,1'-di-tert-butoxycarbonyl-5,5'-bis(tert-butyldiphenylsilanyloxymethyl)-2,3'-bipyrrolidine 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: 55.0%

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

: 930769-31-6
5,5'-bis-(tert-butyl-diphenyl-silanyloxymethyl)-[2,3']bipyrrolidinyl-1'-carboxylic acid tert-butyl ester

: 930769-32-7
1,1'-di-tert-butoxycarbonyl-5,5'-bis(tert-butyldiphenylsilanyloxymethyl)-2,3'-bipyrrolidine

: 930769-30-5
(2R,3'R,5S,5'S)-1,1'-di-tert-butoxycarbonyl-5,5'-bis(tert-butyldiphenylsilanyloxymethyl)-2,3'-bipyrrolidine

: 930769-33-8
1,1'-di-tert-butoxycarbonyl-5,5'-bis(tert-butyldiphenylsilanyloxymethyl)-2,3'-bipyrrolidine

Guidance literature:: (2S,5S/R)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)methyl-5-methoxy-pyrrolidine; With t-butyldimethylsiyl triflate; In tetrahydrofuran; at -15 ℃; for 0.0833333h;

With samarium diiodide; In tetrahydrofuran; at -15 ℃; for 0.0833333h;
DOI:10.1021/jo062406l

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 930769-33-8
1,1'-di-tert-butoxycarbonyl-5,5'-bis(tert-butyldiphenylsilanyloxymethyl)-2,3'-bipyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 99 percent / imidazole / dimethylformamide / 18 h / 20 °C

2.1: 96 percent / DMAP / acetonitrile / 4 h / 20 °C

3.1: 98 percent / LiEt₃BH / tetrahydrofuran / 0.25 h / -80 °C

4.1: 90 percent / 3 Angstroem molecular sieves; BF₃*OEt₂ / diethyl ether / 4.5 h / 20 °C

5.1: TBSOTf / tetrahydrofuran / 0.08 h / -15 °C

5.2: 2.5 percent / SmI₂ / tetrahydrofuran / 0.08 h / -15 °C

With 1H-imidazole; dmap; 3 A molecular sieve; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; lithium triethylborohydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo062406l

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 930769-33-8
1,1'-di-tert-butoxycarbonyl-5,5'-bis(tert-butyldiphenylsilanyloxymethyl)-2,3'-bipyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / DMAP / acetonitrile / 4 h / 20 °C

2.1: 98 percent / LiEt₃BH / tetrahydrofuran / 0.25 h / -80 °C

3.1: 90 percent / 3 Angstroem molecular sieves; BF₃*OEt₂ / diethyl ether / 4.5 h / 20 °C

4.1: TBSOTf / tetrahydrofuran / 0.08 h / -15 °C

4.2: 2.5 percent / SmI₂ / tetrahydrofuran / 0.08 h / -15 °C

With dmap; 3 A molecular sieve; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; lithium triethylborohydride; In tetrahydrofuran; diethyl ether; acetonitrile;
DOI:10.1021/jo062406l