methyl (2S,3S,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-2-propenyl-3-vinylpiperidine-1-carboxylate

Base Information

Chemical Name:methyl (2S,3S,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-2-propenyl-3-vinylpiperidine-1-carboxylate
CAS No.:442202-23-5
Molecular Formula:C₂₉H₃₉NO₃Si
Molecular Weight:477.719
Hs Code.:

Synonyms:methyl (2S,3S,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-2-propenyl-3-vinylpiperidine-1-carboxylate

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Chemical Property of methyl (2S,3S,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-2-propenyl-3-vinylpiperidine-1-carboxylate

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Technology Process of methyl (2S,3S,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-2-propenyl-3-vinylpiperidine-1-carboxylate

There total 8 articles about methyl (2S,3S,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-2-propenyl-3-vinylpiperidine-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:

: 1530-32-1
ethyltriphenylphosphonium bromide

: (2R,3S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-formyl-3-vinyl-piperidine-1-carboxylic acid methyl ester

: 442202-23-5
methyl (2S,3S,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-2-propenyl-3-vinylpiperidine-1-carboxylate

Guidance literature:: ethyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

(2R,3S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-formyl-3-vinyl-piperidine-1-carboxylic acid methyl ester; In tetrahydrofuran; hexane; at 20 ℃; for 2h;
DOI:10.1016/j.tet.2004.05.039

Reference yield:

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

: 442202-23-5
methyl (2S,3S,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-2-propenyl-3-vinylpiperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 7 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

5.1: 96 percent / Super-Hydride / tetrahydrofuran / 1 h / 0 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

7.2: 691 mg / tetrahydrofuran; hexane / 2 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; oxalyl dichloride; methyllithium; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 6.1: Swern oxidation / 7.2: Wittig reaction;
DOI:10.1016/j.tet.2004.05.039

Reference yield:

: 442202-21-3
methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-trifluoromethanesulfonyloxy-3,4-dihydro-2H-pyridine-1-carboxylate

: 442202-23-5
methyl (2S,3S,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-2-propenyl-3-vinylpiperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 88 percent / Pd(PPh₃)4 / dimethylformamide / 15 h / 70 °C

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

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

2.3: 96 percent / diethyl ether / 1 h / -78 - -30 °C

3.1: 96 percent / Super-Hydride / tetrahydrofuran / 1 h / 0 °C

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

5.2: 691 mg / tetrahydrofuran; hexane / 2 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; oxalyl dichloride; methyllithium; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 4.1: Swern oxidation / 5.2: Wittig reaction;
DOI:10.1016/j.tet.2004.05.039