(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

Base Information

• Chemical Name: (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
• CAS No.: 1246937-59-6
• Molecular Formula: C₄₀H₆₃NO₄Si₂
• Molecular Weight: 678.116
• Mol file: 1246937-59-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 17 articles about (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 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: 97.0%

(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) → (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 (1246937-59-6)

Guidance literature:

With potassium carbonate;

DOI:10.1021/jo202119p

Reference yield: 92.0%

(4R,5R,E)-N-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-hydroxy-4-methylocta-2,4-dienyl)-5-hydroxy-4,6-dimethylhept-2-enamide (1246937-58-5) + tert-butylchlorodiphenylsilane (58479-61-1) → (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 (1246937-59-6)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 ℃; for 3h; chemoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201002220

Reference yield:

C6H8N2O2 (159420-55-0) → (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 (1246937-59-6)

Guidance literature:

Multi-step reaction with 5 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: triisopropoxytitanium(IV) chloride; n-butyllithium; cyclopentylmagnesium chloride / diethyl ether / -78 - -30 °C / Inert atmosphere

5.1: 1H-imidazole / dichloromethane / 3 h / 0 °C / Inert atmosphere

With 1H-imidazole; triisopropoxytitanium(IV) chloride; n-butyllithium; dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate); trimethylaluminum; titanium tetrachloride; cyclopentylmagnesium chloride; In diethyl ether; dichloromethane; pentane; 4.1: Negishi coupling reaction;

DOI:10.1021/jo202119p

upstream raw materials:

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

tert-butylchlorodiphenylsilane

C₆H₈N₂O₂

(S)-1-(tert-butyldimethylsilyloxy)hex-4-yn-3-ol

Downstream raw materials:

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

(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