(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

Base Information

• Chemical Name: (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
• CAS No.: 1417560-10-1
• Molecular Formula: C₂₅H₃₄O₄
• Molecular Weight: 398.543
• Mol file: 1417560-10-1.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 7 articles about (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 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:

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 (1417559-96-6) → (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 (1417559-97-7) + (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 (1417560-10-1)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; In tetrahydrofuran; tert-butyl alcohol; at 20 ℃; for 0.2h; Overall yield = 63 %; Overall yield = 113 mg; Optical yield = 32 %de; Inert atmosphere;

DOI:10.1139/v2012-088

Reference yield:

(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) → (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 (1417559-97-7) + (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 (1417560-10-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 0 °C / Inert atmosphere

2: N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide / tetrahydrofuran; tert-butyl alcohol / 0.2 h / 20 °C / Inert atmosphere

With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;

DOI:10.1139/v2012-088

Reference yield:

5-(benzyloxymethyl)-5-(((4R,5R)-5-(2-(tertbutyldimethylsilyloxy)ethyl)-4-isopropyl-5-methylcyclopent-1-enyl)methyl)-4-methyldihydrofuran-2(3H)-one → (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 (1417559-97-7) + (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 (1417560-10-1)

Guidance literature:

Multi-step reaction with 3 steps

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

2: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 0 °C / Inert atmosphere

3: N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide / tetrahydrofuran; tert-butyl alcohol / 0.2 h / 20 °C / Inert atmosphere

With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; hydrogen fluoride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol;

DOI:10.1139/v2012-088

upstream raw materials:

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

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

(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