(4S,5R,6S)-7-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-5-methylhept-1-en-4-ol

Base Information

• Chemical Name: (4S,5R,6S)-7-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-5-methylhept-1-en-4-ol
• CAS No.: 1415934-61-0
• Molecular Formula: C₃₂H₄₂O₄Si
• Molecular Weight: 518.769
• Mol file: 1415934-61-0.mol

Synonyms:(4S,5R,6S)-7-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-5-methylhept-1-en-4-ol

Chemical Property of (4S,5R,6S)-7-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-5-methylhept-1-en-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R,6S)-7-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-5-methylhept-1-en-4-ol

There total 4 articles about (4S,5R,6S)-7-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-5-methylhept-1-en-4-ol 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:

Allyl acetate (591-87-7) + (2R,3S)-4-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-2-methylbutan-1-ol (1331882-90-6) → (4S,5R,6S)-7-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-5-methylhept-1-en-4-ol (1415934-61-0) + (4R,5R,6S)-7-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-5-methylhept-1-en-4-ol (1415934-62-1)

Guidance literature:

With 3,4-dinitrobenzoic acid; C₄₈H₃₇Cl₂IrN₂O₈P₂; caesium carbonate; In tetrahydrofuran; water; at 90 ℃; for 24h; Overall yield = 73 %; Overall yield = 55 mg; diastereoselective reaction; Sealed tube; Inert atmosphere;

DOI:10.1021/ol3030692

Reference yield:

(2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-methylbutan-1-one (1415934-59-6) → (4S,5R,6S)-7-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-5-methylhept-1-en-4-ol (1415934-61-0) + (4R,5R,6S)-7-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-5-methylhept-1-en-4-ol (1415934-62-1)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 3 h / 20 °C / Inert atmosphere

2: 10-camphorsufonic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere

3: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / 0 - 20 °C / Inert atmosphere

4: C₄₈H₃₇Cl₂IrN₂O₈P₂; caesium carbonate; 3,4-dinitrobenzoic acid / tetrahydrofuran; water / 24 h / 90 °C / Sealed tube; Inert atmosphere

With sodium tetrahydroborate; 3,4-dinitrobenzoic acid; C₄₈H₃₇Cl₂IrN₂O₈P₂; 10-camphorsufonic acid; diisobutylaluminium hydride; caesium carbonate; In tetrahydrofuran; ethanol; hexane; dichloromethane; water;

DOI:10.1021/ol3030692

Reference yield:

(2R,3S)-<(tert-butyldiphenylsilyl)oxy>-2-methyl-1,3-butanediol (128329-22-6) → (4S,5R,6S)-7-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-5-methylhept-1-en-4-ol (1415934-61-0) + (4R,5R,6S)-7-(tert-butyldiphenylsilyloxy)-6-(4-methoxybenzyloxy)-5-methylhept-1-en-4-ol (1415934-62-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 10-camphorsufonic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere

2: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / 0 - 20 °C / Inert atmosphere

3: C₄₈H₃₇Cl₂IrN₂O₈P₂; caesium carbonate; 3,4-dinitrobenzoic acid / tetrahydrofuran; water / 24 h / 90 °C / Sealed tube; Inert atmosphere

With 3,4-dinitrobenzoic acid; C₄₈H₃₇Cl₂IrN₂O₈P₂; 10-camphorsufonic acid; diisobutylaluminium hydride; caesium carbonate; In tetrahydrofuran; hexane; dichloromethane; water;

DOI:10.1021/ol3030692

upstream raw materials:

Allyl acetate

(2R,3S)-4-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-2-methylbutan-1-ol

(2S,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-4-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-methylbutan-1-one

(2R,3S)-<(tert-butyldiphenylsilyl)oxy>-2-methyl-1,3-butanediol