(3R,4R,E)-7-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tertbutyldiphenylsilyloxy)-4-methylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate

Base Information

• Chemical Name: (3R,4R,E)-7-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tertbutyldiphenylsilyloxy)-4-methylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate
• CAS No.: 1346661-76-4
• Molecular Formula: C₄₂H₆₅NO₅Si₂
• Molecular Weight: 720.153
• Mol file: 1346661-76-4.mol

Synonyms:(3R,4R,E)-7-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tertbutyldiphenylsilyloxy)-4-methylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate

Chemical Property of (3R,4R,E)-7-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tertbutyldiphenylsilyloxy)-4-methylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,E)-7-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tertbutyldiphenylsilyloxy)-4-methylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate

There total 8 articles about (3R,4R,E)-7-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tertbutyldiphenylsilyloxy)-4-methylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate 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: 92.0%

(3R,4R,E)-7-((E)-3-iodoallylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate (1346661-73-1) + (S,E)-1-(tert-butyl(1-(tert-butyldimethylsilyloxy)-5-iodohex-4-en-3-yloxy)(phenyl)silyl)benzene (1346661-60-6) → (3R,4R,E)-7-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tertbutyldiphenylsilyloxy)-4-methylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate (1346661-76-4)

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;

(3R,4R,E)-7-((E)-3-iodoallylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; pentane; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo202119p

Reference yield:

C6H8N2O2 (159420-55-0) → (3R,4R,E)-7-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tertbutyldiphenylsilyloxy)-4-methylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate (1346661-76-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate) / pentane / 24 h / -75 °C / Molecular sieve; Inert atmosphere

2.1: titanium tetrachloride / dichloromethane / 72 h / -20 °C / Inert atmosphere

3.1: trimethylaluminum / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

3.2: 5 h / Inert atmosphere; Reflux

4.1: pyridine; dmap / dichloromethane / Inert atmosphere

5.1: n-butyllithium; tri-n-butyl-tin hydride; copper(l) cyanide / tetrahydrofuran; hexane / 3 h / -78 °C / Inert atmosphere

5.2: 0.33 h / 0 °C / Inert atmosphere

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

6.2: 0.33 h / -78 °C / Inert atmosphere

6.3: Inert atmosphere

With pyridine; dmap; n-butyllithium; dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate); trimethylaluminum; tert.-butyl lithium; tri-n-butyl-tin hydride; copper(l) cyanide; titanium tetrachloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; pentane; 6.3: Negishi cross-coupling;

DOI:10.1021/jo202119p

Reference yield:

methyl (2S,3E)-2-(dimethyl(phenyl)silyl)pent-3-enoate → (3R,4R,E)-7-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tertbutyldiphenylsilyloxy)-4-methylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate (1346661-76-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: titanium tetrachloride / dichloromethane / 72 h / -20 °C / Inert atmosphere

2.1: trimethylaluminum / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.2: 5 h / Inert atmosphere; Reflux

3.1: pyridine; dmap / dichloromethane / Inert atmosphere

4.1: n-butyllithium; tri-n-butyl-tin hydride; copper(l) cyanide / tetrahydrofuran; hexane / 3 h / -78 °C / Inert atmosphere

4.2: 0.33 h / 0 °C / Inert atmosphere

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

5.2: 0.33 h / -78 °C / Inert atmosphere

5.3: Inert atmosphere

With pyridine; dmap; n-butyllithium; trimethylaluminum; tert.-butyl lithium; tri-n-butyl-tin hydride; copper(l) cyanide; titanium tetrachloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; pentane; 5.3: Negishi cross-coupling;

DOI:10.1021/jo202119p

upstream raw materials:

C₆H₈N₂O₂

(4R,5R,E)-methyl 5-(benzyloxy)-4,6-dimethylhept-2-enoate

(3R,4R,E)-7-((E)-3-iodoallylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate

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

Downstream raw materials:

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

(R)-((3R,4R,E)-7-((S,2E,4E)-6-(tert-butyldiphenylsilyloxy)-4-methyl-8-oxoocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl) 1-(2-(chloromethyl)oxazole-4-carbonyl)pyrrolidine-2-carboxylate

C₄₄H₅₇N₃O₇Si

C₄₄H₅₇N₃O₇Si