(2S,5S,2'S,5'S,2''S,5''S)-2,5''-bis-[(tert-butyldiphenylsilyloxy)methyl]-dodecahydro-terpyrrole

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Chemical Name:(2S,5S,2'S,5'S,2''S,5''S)-2,5''-bis-[(tert-butyldiphenylsilyloxy)methyl]-dodecahydro-terpyrrole
CAS No.:782496-08-6
Molecular Formula:C₄₆H₆₃N₃O₂Si₂
Molecular Weight:746.196
Hs Code.:

Synonyms:(2S,5S,2'S,5'S,2''S,5''S)-2,5''-bis-[(tert-butyldiphenylsilyloxy)methyl]-dodecahydro-terpyrrole

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Chemical Property of (2S,5S,2'S,5'S,2''S,5''S)-2,5''-bis-[(tert-butyldiphenylsilyloxy)methyl]-dodecahydro-terpyrrole

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Technology Process of (2S,5S,2'S,5'S,2''S,5''S)-2,5''-bis-[(tert-butyldiphenylsilyloxy)methyl]-dodecahydro-terpyrrole

There total 16 articles about (2S,5S,2'S,5'S,2''S,5''S)-2,5''-bis-[(tert-butyldiphenylsilyloxy)methyl]-dodecahydro-terpyrrole 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%

: 782496-07-5
(2S,5S,2'S,5'S,2''S,5''S)-N,N',N''-tri-tert-butoxycarbonyl-2,5''-bis-[(tert-butyldiphenylsilyloxy)methyl]-dodecahydro-terpyrrole

: 782496-08-6
(2S,5S,2'S,5'S,2''S,5''S)-2,5''-bis-[(tert-butyldiphenylsilyloxy)methyl]-dodecahydro-terpyrrole

Guidance literature:: (2S,5S,2'S,5'S,2''S,5''S)-N,N',N''-tri-tert-butoxycarbonyl-2,5''-bis-[(tert-butyldiphenylsilyloxy)methyl]-dodecahydro-terpyrrole; 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:

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

: 782496-08-6
(2S,5S,2'S,5'S,2''S,5''S)-2,5''-bis-[(tert-butyldiphenylsilyloxy)methyl]-dodecahydro-terpyrrole

Guidance literature:: Multi-step reaction with 15 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

8.1: 92 percent / H₂ / Pt/C / methanol / 16 h / 760 Torr

9.1: 99 percent / SOCl₂; NEt₃ / CH₂Cl₂ / 0.33 h / -20 °C

10.1: 96 percent / aq. NaIO₄ / RuCl₃ / CCl₄; acetonitrile / 0.5 h / 0 °C

11.1: LiN₃ / dimethylformamide; hexamethylphosphoric acid triamide / 40 h / 20 °C

11.2: 73 percent / aq. H₂SO₄ / tetrahydrofuran / 12 h / 0 °C / pH 2

12.1: NEt₃ / CH₂Cl₂ / 2 h / -25 - 0 °C

13.1: 1.02 g / H₂ / Pd/C / tetrahydrofuran; methanol / 6 h / 760 Torr

14.1: 57 percent / NEt₃ / dimethylformamide / 24 h / 20 °C

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

15.2: 98 percent / aq. Na₃PO₄ / CH₂Cl₂ / pH 12

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; n-butyllithium; thionyl chloride; lithium azide; trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether; camphor-10-sulfonic acid; hydrogen; diisobutylaluminium hydride; potassium carbonate; triethylamine; ruthenium trichloride; palladium on activated charcoal; platinum on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; Petroleum ether;
DOI:10.1002/chem.200400181

Reference yield:

: 192389-28-9
(2S,5S)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)-methyl-pyrrolidine-5-carbaldehyde

: 782496-08-6
(2S,5S,2'S,5'S,2''S,5''S)-2,5''-bis-[(tert-butyldiphenylsilyloxy)methyl]-dodecahydro-terpyrrole

Guidance literature:: Multi-step reaction with 13 steps

1.1: tetrahydrofuran / 4 h / -40 - 0 °C

2.1: 97 percent / aq. K₂CO₃ / tetrahydrofuran; methanol / 4 h

3.1: 97 percent / imidazole / CH₂Cl₂ / 0.5 h / 0 °C

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

4.2: 54 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1.5 h / -80 - -70 °C

5.1: 94 percent / CSA / tetrahydrofuran; methanol / 0.25 h / -10 °C

6.1: 92 percent / H₂ / Pt/C / methanol / 16 h / 760 Torr

7.1: 99 percent / SOCl₂; NEt₃ / CH₂Cl₂ / 0.33 h / -20 °C

8.1: 96 percent / aq. NaIO₄ / RuCl₃ / CCl₄; acetonitrile / 0.5 h / 0 °C

9.1: LiN₃ / dimethylformamide; hexamethylphosphoric acid triamide / 40 h / 20 °C

9.2: 73 percent / aq. H₂SO₄ / tetrahydrofuran / 12 h / 0 °C / pH 2

10.1: NEt₃ / CH₂Cl₂ / 2 h / -25 - 0 °C

11.1: 1.02 g / H₂ / Pd/C / tetrahydrofuran; methanol / 6 h / 760 Torr

12.1: 57 percent / NEt₃ / dimethylformamide / 24 h / 20 °C

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

13.2: 98 percent / aq. Na₃PO₄ / CH₂Cl₂ / pH 12

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; n-butyllithium; thionyl chloride; lithium azide; trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether; camphor-10-sulfonic acid; hydrogen; potassium carbonate; triethylamine; ruthenium trichloride; palladium on activated charcoal; platinum on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/chem.200400181