(4R,5R,E)-5-(benzyloxy)-N-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienyl)-4,6-dimethylhept-2-enamide

Base Information

Chemical Name:(4R,5R,E)-5-(benzyloxy)-N-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienyl)-4,6-dimethylhept-2-enamide
CAS No.:1346661-74-2
Molecular Formula:C₄₇H₆₉NO₄Si₂
Molecular Weight:768.24
Hs Code.:

(4R,5R,E)-5-(benzyloxy)-N-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienyl)-4,6-dimethylhept-2-enamide

Synonyms:(4R,5R,E)-5-(benzyloxy)-N-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienyl)-4,6-dimethylhept-2-enamide

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Chemical Property of (4R,5R,E)-5-(benzyloxy)-N-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienyl)-4,6-dimethylhept-2-enamide

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Technology Process of (4R,5R,E)-5-(benzyloxy)-N-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienyl)-4,6-dimethylhept-2-enamide

There total 3 articles about (4R,5R,E)-5-(benzyloxy)-N-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienyl)-4,6-dimethylhept-2-enamide 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: 93.0%

: 1346661-72-0
C₁₉H₂₆INO₂

: 1346661-60-6
(S,E)-1-(tert-butyl(1-(tert-butyldimethylsilyloxy)-5-iodohex-4-en-3-yloxy)(phenyl)silyl)benzene

: 1346661-74-2
(4R,5R,E)-5-(benzyloxy)-N-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienyl)-4,6-dimethylhept-2-enamide

Guidance literature:: (S,E)-1-(tert-butyl(1-(tert-butyldimethylsilyloxy)-5-iodohex-4-en-3-yloxy)(phenyl)silyl)benzene; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 0.5h; Inert atmosphere;

With zinc(II) chloride; In tetrahydrofuran; diethyl ether; pentane; at -78 ℃; for 0.333333h; Inert atmosphere;

C₁₉H₂₆INO₂; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; pentane; regioselective reaction; Inert atmosphere;
DOI:10.1021/jo202119p

Reference yield:

: 1246937-70-1
C₁₉H₂₅NO₂

: 1346661-74-2
(4R,5R,E)-5-(benzyloxy)-N-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienyl)-4,6-dimethylhept-2-enamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium; tri-n-butyl-tin hydride; copper(l) cyanide / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere

2.2: 0.33 h / -78 °C / Inert atmosphere

2.3: Inert atmosphere

With n-butyllithium; tert.-butyl lithium; tri-n-butyl-tin hydride; copper(l) cyanide; In diethyl ether; pentane; 2.3: Negishi cross-coupling;
DOI:10.1021/jo202119p

Reference yield:

: C₂₈H₄₂O₂Si₂

: 1346661-74-2
(4R,5R,E)-5-(benzyloxy)-N-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienyl)-4,6-dimethylhept-2-enamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: Schwartz's reagent / tetrahydrofuran / 1.5 h / Inert atmosphere; Darkness

1.2: 0.17 h / 0 °C / Inert atmosphere

2.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere

2.2: 0.33 h / -78 °C / Inert atmosphere

2.3: Inert atmosphere

With Schwartz's reagent; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; pentane; 2.3: Negishi cross-coupling;
DOI:10.1021/jo202119p