(-)-(E)-methyl 4-((2S,3R,6S)-6-(2-((tert-butyl)diphenylsilyloxy)ethyl)-3-methyl-1-tosylpiperidin-2-yl)but-2-enoate

Base Information

Chemical Name:(-)-(E)-methyl 4-((2S,3R,6S)-6-(2-((tert-butyl)diphenylsilyloxy)ethyl)-3-methyl-1-tosylpiperidin-2-yl)but-2-enoate
CAS No.:1334404-58-8
Molecular Formula:C₃₆H₄₇NO₅SSi
Molecular Weight:633.924
Hs Code.:

Synonyms:(-)-(E)-methyl 4-((2S,3R,6S)-6-(2-((tert-butyl)diphenylsilyloxy)ethyl)-3-methyl-1-tosylpiperidin-2-yl)but-2-enoate

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Chemical Property of (-)-(E)-methyl 4-((2S,3R,6S)-6-(2-((tert-butyl)diphenylsilyloxy)ethyl)-3-methyl-1-tosylpiperidin-2-yl)but-2-enoate

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Technology Process of (-)-(E)-methyl 4-((2S,3R,6S)-6-(2-((tert-butyl)diphenylsilyloxy)ethyl)-3-methyl-1-tosylpiperidin-2-yl)but-2-enoate

There total 10 articles about (-)-(E)-methyl 4-((2S,3R,6S)-6-(2-((tert-butyl)diphenylsilyloxy)ethyl)-3-methyl-1-tosylpiperidin-2-yl)but-2-enoate 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:

: 1334404-57-7
C₃₂H₄₃NO₄SSi

: 85636-50-6
1-(trimethylsiloxy)-1-methoxy-1,3-butadiene

: 1334404-58-8
(-)-(E)-methyl 4-((2S,3R,6S)-6-(2-((tert-butyl)diphenylsilyloxy)ethyl)-3-methyl-1-tosylpiperidin-2-yl)but-2-enoate

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -85 ℃; optical yield given as %de;
DOI:10.1039/c1cc13048j

Reference yield:

: 934472-06-7
2-hydroxyethyl-1-(toluene-4-sulfonyl)aziridine

: 1334404-58-8
(-)-(E)-methyl 4-((2S,3R,6S)-6-(2-((tert-butyl)diphenylsilyloxy)ethyl)-3-methyl-1-tosylpiperidin-2-yl)but-2-enoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 1H-imidazole / tetrahydrofuran / 0 - 20 °C

2.1: copper(I) bromide dimethylsulfide complex / 2,3-dimercapto-succinic acid / 1 h / -78 °C

2.2: -78 - 20 °C

3.1: trifluoroacetic acid / acetone / 20 °C

4.1: diethylzinc / hexane; toluene / 60 h / 0 °C

5.1: N-iodo-succinimide / 3 h / 20 °C / Inert atmosphere

6.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / Reflux

7.1: boron trifluoride diethyl etherate / dichloromethane / -85 °C

With 1H-imidazole; N-iodo-succinimide; copper(I) bromide dimethylsulfide complex; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; diethylzinc; tri-n-butyl-tin hydride; trifluoroacetic acid; In tetrahydrofuran; 2,3-dimercapto-succinic acid; hexane; dichloromethane; acetone; toluene;
DOI:10.1039/c1cc13048j

Reference yield:

: 1334404-45-3
2-[2-((tert-butyl)diphenylsilanyloxy)ethyl]-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine

: 1334404-58-8
(-)-(E)-methyl 4-((2S,3R,6S)-6-(2-((tert-butyl)diphenylsilyloxy)ethyl)-3-methyl-1-tosylpiperidin-2-yl)but-2-enoate

Guidance literature:: Multi-step reaction with 4 steps

1: diethylzinc / hexane; toluene / 60 h / 0 °C

2: N-iodo-succinimide / 3 h / 20 °C / Inert atmosphere

3: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / Reflux

4: boron trifluoride diethyl etherate / dichloromethane / -85 °C

With N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; diethylzinc; tri-n-butyl-tin hydride; In hexane; dichloromethane; toluene;
DOI:10.1039/c1cc13048j