(2S,3R)-1-benzyl-2-((tert-butyldiphenylsilyloxy)methyl)-3-phenoxy-1,2,3,6-tetrahydropyridine

Base Information

Chemical Name:(2S,3R)-1-benzyl-2-((tert-butyldiphenylsilyloxy)methyl)-3-phenoxy-1,2,3,6-tetrahydropyridine
CAS No.:1313436-06-4
Molecular Formula:C₃₅H₃₉NO₂Si
Molecular Weight:533.786
Hs Code.:

Synonyms:(2S,3R)-1-benzyl-2-((tert-butyldiphenylsilyloxy)methyl)-3-phenoxy-1,2,3,6-tetrahydropyridine

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Chemical Property of (2S,3R)-1-benzyl-2-((tert-butyldiphenylsilyloxy)methyl)-3-phenoxy-1,2,3,6-tetrahydropyridine

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Technology Process of (2S,3R)-1-benzyl-2-((tert-butyldiphenylsilyloxy)methyl)-3-phenoxy-1,2,3,6-tetrahydropyridine

There total 4 articles about (2S,3R)-1-benzyl-2-((tert-butyldiphenylsilyloxy)methyl)-3-phenoxy-1,2,3,6-tetrahydropyridine 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: 87.0%

: (S)-1-((S)-1-benzyl-2,5-dihydro-1H-pyrrol-2-yl)-2-(tert-butyldiphenylsilyloxy)ethanol

: 139-02-6
sodium phenoxide

: 1313436-06-4
(2S,3R)-1-benzyl-2-((tert-butyldiphenylsilyloxy)methyl)-3-phenoxy-1,2,3,6-tetrahydropyridine

Guidance literature:: sodium phenoxide; With 15-crown-5; In tetrahydrofuran; at -15 ℃; Inert atmosphere;

(S)-1-((S)-1-benzyl-2,5-dihydro-1H-pyrrol-2-yl)-2-(tert-butyldiphenylsilyloxy)ethanol; With trifluoromethylsulfonic anhydride; In tetrahydrofuran; dichloromethane; at -15 - 20 ℃; Inert atmosphere;
DOI:10.1021/ol201349k

Reference yield:

: 1313435-98-1
(S)-1-((S)-1-benzyl-2,5-dihydro-1H-pyrrol-2-yl)ethane-1,2-diol

: 1313436-06-4
(2S,3R)-1-benzyl-2-((tert-butyldiphenylsilyloxy)methyl)-3-phenoxy-1,2,3,6-tetrahydropyridine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1H-imidazole / dichloromethane / Inert atmosphere; Cooling with ice

2.1: 15-crown-5 / tetrahydrofuran / -15 °C / Inert atmosphere

2.2: proton sponge / -15 - 20 °C / Inert atmosphere

With 1H-imidazole; 15-crown-5; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol201349k

Reference yield:

: 4383-22-6
Allylbenzylamine

: 1313436-06-4
(2S,3R)-1-benzyl-2-((tert-butyldiphenylsilyloxy)methyl)-3-phenoxy-1,2,3,6-tetrahydropyridine

Guidance literature:: Multi-step reaction with 4 steps

1.1: sulfuric acid / ethanol; water / 0.17 h / 20 °C

1.2: 16 h / pH 8 / Reflux

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 16 h / Inert atmosphere; Reflux

3.1: 1H-imidazole / dichloromethane / Inert atmosphere; Cooling with ice

4.1: 15-crown-5 / tetrahydrofuran / -15 °C / Inert atmosphere

4.2: proton sponge / -15 - 20 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 15-crown-5; sulfuric acid; In tetrahydrofuran; ethanol; dichloromethane; water;
DOI:10.1021/ol201349k