(R)-5-( (benzyloxy)methyl)-5-(((4R,5R)-5-(2-hydroxyethyl)-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-hydroxyethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)-4-methylfuran-2(5H)-one
• CAS No.: 1417559-94-4
• Molecular Formula: C₂₅H₃₄O₄
• Molecular Weight: 398.543
• Mol file: 1417559-94-4.mol

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (R)-5-( (benzyloxy)methyl)-5-(((4R,5R)-5-(2-hydroxyethyl)-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: 96.0%

(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) → (R)-5-( (benzyloxy)methyl)-5-(((4R,5R)-5-(2-hydroxyethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)-4-methylfuran-2(5H)-one (1417559-94-4)

Guidance literature:

With hydrogen fluoride; water; In acetonitrile; for 0.25h; Inert atmosphere;

DOI:10.1021/acs.joc.5b00355

Reference yield:

5-(benzyloxymethyl)-5-(((4R,5R)-5-(2-(tertbutyldimethylsilyloxy)ethyl)-4-isopropyl-5-methylcyclopent-1-enyl)methyl)-4-methyldihydrofuran-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 (1417559-94-4) + (S)-5-((benzyloxy)methyl)-5-(((4R,5R)-5-(2-hydroxyethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)-4-methylfuran-2(5H)-one (1417559-95-5)

Guidance literature:

With hydrogen fluoride; In water; acetonitrile; for 0.25h; Overall yield = 91 %; Overall yield = 34.8 mg; 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-hydroxyethyl)-4-isopropyl-5-methylcyclopent-1-en-1-yl)methyl)-4-methylfuran-2(5H)-one (1417559-94-4)

Guidance literature:

Multi-step reaction with 3 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

3.1: hydrogen fluoride; water / acetonitrile / 0.25 h / Inert atmosphere

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

DOI:10.1021/acs.joc.5b00355

upstream raw materials:

(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

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

(3aR,5aR,6R,9aR)-9a-((benzyloxy)methyl)-6-isopropyl-3a,5a-dimethyl-3,3a,5,5a,6,7,9,9a-octahydroazuleno[5,6-b]furan-2,4-dione

(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