(R)-5-( (benzyloxy)methyl)-5-( ((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)-4-methylfuran-2(5H)-one

Base Information

• Chemical Name: (R)-5-( (benzyloxy)methyl)-5-( ((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)-4-methylfuran-2(5H)-one
• CAS No.: 1417559-92-2
• Molecular Formula: C₃₁H₄₈O₄Si
• Molecular Weight: 512.805

Synonyms:(R)-5-( (benzyloxy)methyl)-5-( ((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)-4-methylfuran-2(5H)-one

Chemical Property of (R)-5-( (benzyloxy)methyl)-5-( ((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)-4-methylfuran-2(5H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (R)-5-( (benzyloxy)methyl)-5-( ((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)-4-methylfuran-2(5H)-one

There total 3 articles about (R)-5-( (benzyloxy)methyl)-5-( ((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)-4-methylfuran-2(5H)-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:

C37H54O4SeSi (1417608-62-8) → (S)-5-(benzyloxymethyl)-5-(((4R,5R)-5-(2-(tert-butyldimethylsilyloxy)ethyl)-4-isopropyl-5-methylcyclopent-1-enyl)methyl)-4-methylfuran-2(5H)-one (1417559-93-3) + (R)-5-( (benzyloxy)methyl)-5-( ((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)-4-methylfuran-2(5H)-one (1417559-92-2)

Guidance literature:

C₃₇H₅₄O₄SeSi; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;

With triethylamine; In dichloromethane; at 20 ℃; Overall yield = 75 %; Overall yield = 55.4 mg; Optical yield = 16 %de; Inert atmosphere;

DOI:10.1139/v2012-088

Reference yield:

(R)-1-(benzyloxy)-2-(((4R,5R)-5-(2-((tert-butyldimethylsilyl)-oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)-3-methylbut-3-en-2-ol → (R)-5-( (benzyloxy)methyl)-5-( ((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)-4-methylfuran-2(5H)-one (1417559-92-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: isopropylmagnesium chloride / tetrahydrofuran; diethyl ether / 1 h / 0 - 22 °C / Inert atmosphere

1.2: 16 h / 20 °C / Inert atmosphere

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 7.5 h / 70 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; isopropylmagnesium chloride; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1021/acs.joc.5b00355

Reference yield:

(2-((1R,5R)-2-((2-((benzyloxy)methyl)-3-(bromomethyl)-3-methyloxiran-2-yl)methyl)-5-isopropyl-1-methylcyclopent-2-en-1-yl)ethoxy)(tert-butyl)dimethylsilane → (R)-5-( (benzyloxy)methyl)-5-( ((4R,5R)-5-(2-((tertbutyldimethylsilyl)oxy)ethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)-4-methylfuran-2(5H)-one (1417559-92-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / -100 - -78 °C / Inert atmosphere

2.1: isopropylmagnesium chloride / tetrahydrofuran; diethyl ether / 1 h / 0 - 22 °C / Inert atmosphere

2.2: 16 h / 20 °C / Inert atmosphere

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 7.5 h / 70 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; n-butyllithium; isopropylmagnesium chloride; In tetrahydrofuran; diethyl ether; hexane; toluene;

DOI:10.1021/acs.joc.5b00355

upstream raw materials:

C₃₇H₅₄O₄SeSi

Downstream raw materials:

2-((1R,5R)-2-(((R)-2-((benzyloxy)methyl)-3-methyl-5-oxo-2,5-dihydrofuran-2-yl)methyl)-5-isopropyl-1-methylcyclopent-2-en-1-yl)acetaldehyde

(3aS,4R,5aR,6R,9aR)-9a-(benzyloxymethyl)-4-hydroxy-6-isopropyl-3a,5a-dimethyl-3a,4,5,5a,6,7,9,9a-octahydroazuleno-[5,6-b]furan-2(3H)-one

(3aS,4S,5aR,6R,9aR)-9a-(benzyloxymethyl)-4-hydroxy-6-isopropyl-3a,5a-dimethyl-3a,4,5,5a,6,7,9,9a-octahydroazuleno-[5,6-b]furan-2(3H)-one

(R)-5-( (benzyloxy)methyl)-5-(((4R,5R)-5-(2-hydroxyethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)-4-methylfuran-2(5H)-one

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