(2R,3R,6S)-benzyl 3-butyl-6-(tert-butyldiphenylsilanyloxymethyl)-2-(2-ethoxycarbonylvinyl)-piperidine-1-carboxylate

Base Information

Chemical Name:(2R,3R,6S)-benzyl 3-butyl-6-(tert-butyldiphenylsilanyloxymethyl)-2-(2-ethoxycarbonylvinyl)-piperidine-1-carboxylate
CAS No.:934186-43-3
Molecular Formula:C₃₉H₅₁NO₅Si
Molecular Weight:641.923
Hs Code.:

Synonyms:(2R,3R,6S)-benzyl 3-butyl-6-(tert-butyldiphenylsilanyloxymethyl)-2-(2-ethoxycarbonylvinyl)-piperidine-1-carboxylate

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Chemical Property of (2R,3R,6S)-benzyl 3-butyl-6-(tert-butyldiphenylsilanyloxymethyl)-2-(2-ethoxycarbonylvinyl)-piperidine-1-carboxylate

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Technology Process of (2R,3R,6S)-benzyl 3-butyl-6-(tert-butyldiphenylsilanyloxymethyl)-2-(2-ethoxycarbonylvinyl)-piperidine-1-carboxylate

There total 2 articles about (2R,3R,6S)-benzyl 3-butyl-6-(tert-butyldiphenylsilanyloxymethyl)-2-(2-ethoxycarbonylvinyl)-piperidine-1-carboxylate 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:

: 875584-45-5
1-phenylmethyl 2-methyl 6-(tert-butyldiphenylsilyloxymethyl)-5,6-dihydro-4H-pyridine-1,2-dicarboxylate

: 934186-43-3
(2R,3R,6S)-benzyl 3-butyl-6-(tert-butyldiphenylsilanyloxymethyl)-2-(2-ethoxycarbonylvinyl)-piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 96 percent / CuI / diethyl ether; hexane / 1 h / -78 - -10 °C

2.1: 95 percent / lithium triethylborohydride / tetrahydrofuran / 2 h / 0 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

3.2: 87 percent / NaH / tetrahydrofuran / 20 h / 20 °C

With copper(l) iodide; oxalyl dichloride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 3.1: Swern oxidation / 3.2: Horner-Emmons reaction;
DOI:10.3987/COM-06-S(W)6

Reference yield:

: 934186-41-1
(2R,3R,6S)-(-)-1-benzyl 2-methyl 3-butyl-6-(tert-butyldiphenylsilanyloxymethyl)piperidine-1,2-dicarboxylate

: 934186-43-3
(2R,3R,6S)-benzyl 3-butyl-6-(tert-butyldiphenylsilanyloxymethyl)-2-(2-ethoxycarbonylvinyl)-piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 95 percent / lithium triethylborohydride / tetrahydrofuran / 2 h / 0 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

2.2: 87 percent / NaH / tetrahydrofuran / 20 h / 20 °C

With oxalyl dichloride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation / 2.2: Horner-Emmons reaction;
DOI:10.3987/COM-06-S(W)6

Reference yield: 65.0%

: 934186-43-3
(2R,3R,6S)-benzyl 3-butyl-6-(tert-butyldiphenylsilanyloxymethyl)-2-(2-ethoxycarbonylvinyl)-piperidine-1-carboxylate

: 934186-44-4
(5S,8R,8aS)-(-)-8-butyl-5-(tert-butyldiphenylsilanyloxymethyl)octahydroindolizin-3-one

Guidance literature:: (2R,3R,6S)-benzyl 3-butyl-6-(tert-butyldiphenylsilanyloxymethyl)-2-(2-ethoxycarbonylvinyl)-piperidine-1-carboxylate; With hydrogen; palladium dihydroxide; In methanol; for 44h; under 760.051 Torr;

With triethylaluminum; In dichloromethane; toluene; for 15h; Further stages.; Heating;
DOI:10.3987/COM-06-S(W)6