dimethyl (2R,3S,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-3-vinyl-piperidine-1,2-dicarboxylate

Base Information

Chemical Name:dimethyl (2R,3S,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-3-vinyl-piperidine-1,2-dicarboxylate
CAS No.:442202-22-4
Molecular Formula:C₂₈H₃₇NO₅Si
Molecular Weight:495.691
Hs Code.:

Synonyms:dimethyl (2R,3S,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-3-vinyl-piperidine-1,2-dicarboxylate

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Chemical Property of dimethyl (2R,3S,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-3-vinyl-piperidine-1,2-dicarboxylate

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Technology Process of dimethyl (2R,3S,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-3-vinyl-piperidine-1,2-dicarboxylate

There total 4 articles about dimethyl (2R,3S,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-3-vinyl-piperidine-1,2-dicarboxylate 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: 96.0%

: 1112-56-7
tetravinyltin (IV)

: 442202-05-3
dimethyl (S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5,6-dihydro-4H-pyridine-1,2-dicarboxylate

: 442202-22-4
dimethyl (2R,3S,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-3-vinyl-piperidine-1,2-dicarboxylate

Guidance literature:: tetravinyltin (IV); With methyllithium; In diethyl ether; at 0 ℃; for 0.5h;

With copper(l) iodide; In diethyl ether; at -78 - -35 ℃; for 0.333333h;

dimethyl (S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5,6-dihydro-4H-pyridine-1,2-dicarboxylate; In diethyl ether; at -78 - -30 ℃; for 1h;
DOI:10.1016/j.tet.2004.05.039

Reference yield: 96.0%

: 917-57-7
vinyllithium

: 442202-05-3
dimethyl (S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5,6-dihydro-4H-pyridine-1,2-dicarboxylate

: 442202-22-4
dimethyl (2R,3S,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-3-vinyl-piperidine-1,2-dicarboxylate

Guidance literature:: vinyllithium; With copper(l) iodide; In diethyl ether; at -78 - -35 ℃; for 0.333333h;

dimethyl (S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5,6-dihydro-4H-pyridine-1,2-dicarboxylate; In diethyl ether; at -78 - -30 ℃; for 1h; Further stages.;
DOI:10.1021/ol025775m

Reference yield:

: 209257-75-0
(S)-6-((tert-butyldiphenylsilyloxy)methyl)piperidin-2-one

: 442202-22-4
dimethyl (2R,3S,6S)-(+)-6-(tert-butyldiphenylsilyloxymethyl)-3-vinyl-piperidine-1,2-dicarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 98 percent / tetrahydrofuran; hexane / 2 h / -78 - 0 °C

2.1: hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 96 percent / tetrahydrofuran; hexane / 1 h / -78 - -40 °C

3.1: 88 percent / Pd(PPh₃)4 / dimethylformamide / 15 h / 70 °C

4.1: MeLi / diethyl ether / 0.5 h / 0 °C

4.2: CuI / diethyl ether / 0.33 h / -78 - -35 °C

4.3: 96 percent / diethyl ether / 1 h / -78 - -30 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; methyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.05.039