(4S,6S)-4-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)octa-1,7-dien-3-one

Base Information

• Chemical Name: (4S,6S)-4-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)octa-1,7-dien-3-one
• CAS No.: 1313275-49-8
• Molecular Formula: C₂₂H₃₄O₄Si
• Molecular Weight: 390.595
• Mol file: 1313275-49-8.mol

Synonyms:(4S,6S)-4-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)octa-1,7-dien-3-one

Chemical Property of (4S,6S)-4-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)octa-1,7-dien-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,6S)-4-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)octa-1,7-dien-3-one

There total 5 articles about (4S,6S)-4-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)octa-1,7-dien-3-one 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: 84.0%

(2S,4S)-2-(tert-butyldimethylsilyloxy)-N-methoxy-4[(4-methoxybenzyl)oxy]-N-methylhex-5-enamide (1313275-22-7) + vinyl magnesium bromide (1826-67-1) → (4S,6S)-4-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)octa-1,7-dien-3-one (1313275-49-8)

Guidance literature:

(2S,4S)-2-(tert-butyldimethylsilyloxy)-N-methoxy-4[(4-methoxybenzyl)oxy]-N-methylhex-5-enamide; vinyl magnesium bromide; In tetrahydrofuran; at 0 ℃; for 2h;

With water; ammonium chloride; In tetrahydrofuran;

Reference yield:

(2S)-2-(tert-butyldimethylsilyloxy)-N-methoxy-N-methyl-4-oxobutanamide (1313275-21-6) → (4S,6S)-4-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)octa-1,7-dien-3-one (1313275-49-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: C₁₃H₁₈NO₂^(1-)*Li⁽¹⁺⁾ / toluene; hexane / 1.33 h / 0 °C / Inert atmosphere

1.2: 6 h / -70 - 10 °C

2.1: scandium tris(trifluoromethanesulfonate) / dichloromethane / 0.5 h / 23 °C

3.1: tetrahydrofuran / 2 h / 0 °C

With C₁₃H₁₈NO₂^(1-)*Li⁽¹⁺⁾; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; hexane; dichloromethane; toluene;

Reference yield:

(3S)-3-[(1,1-Dimethylethyl)dimethylsilyloxy]-oxolan-2-one (164264-14-6,669000-31-1) → (4S,6S)-4-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)octa-1,7-dien-3-one (1313275-49-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetrahydrofuran / 23 °C / Inert atmosphere

1.2: 0.75 h / -15 - -8 °C

2.1: sodium hydrogencarbonate; sodium hypochlorite / potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; water / 0.25 h / 23 °C

3.1: C₁₃H₁₈NO₂^(1-)*Li⁽¹⁺⁾ / toluene; hexane / 1.33 h / 0 °C / Inert atmosphere

3.2: 6 h / -70 - 10 °C

4.1: scandium tris(trifluoromethanesulfonate) / dichloromethane / 0.5 h / 23 °C

5.1: tetrahydrofuran / 2 h / 0 °C

With C₁₃H₁₈NO₂^(1-)*Li⁽¹⁺⁾; sodium hypochlorite; sodium hydrogencarbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; hexane; dichloromethane; water; toluene;

upstream raw materials:

(2S,4S)-2-(tert-butyldimethylsilyloxy)-N-methoxy-4[(4-methoxybenzyl)oxy]-N-methylhex-5-enamide

vinyl magnesium bromide

(3S)-3-[(1,1-Dimethylethyl)dimethylsilyloxy]-oxolan-2-one

(2S)-2-(tert-butyldimethylsilyloxy)-4-hydroxy-N-methoxy-N-methylbutanamide

Downstream raw materials:

6-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-cyclohex-2-enone

C₃₅H₄₆O₈Si

C₃₃H₄₂O₉Si

C₃₁H₃₈O₈Si