(3S,4R,5R)-3-[(S)-1-hydroxyethyl]-5-{(1R,2S,5R)-[2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one

Base Information

• Chemical Name: (3S,4R,5R)-3-[(S)-1-hydroxyethyl]-5-{(1R,2S,5R)-[2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one
• CAS No.: 1449307-00-9
• Molecular Formula: C₁₉H₃₂O₆
• Molecular Weight: 356.459
• Mol file: 1449307-00-9.mol

Synonyms:(3S,4R,5R)-3-[(S)-1-hydroxyethyl]-5-{(1R,2S,5R)-[2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one

Chemical Property of (3S,4R,5R)-3-[(S)-1-hydroxyethyl]-5-{(1R,2S,5R)-[2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5R)-3-[(S)-1-hydroxyethyl]-5-{(1R,2S,5R)-[2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one

There total 4 articles about (3S,4R,5R)-3-[(S)-1-hydroxyethyl]-5-{(1R,2S,5R)-[2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-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: 45.0%

(3R,4S,5R)-5-{(1R,2S,5R)-[2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-3-(trimethylsilyl)-4,5-dihydro-3H-furan-2-one (1449307-06-5) + acetaldehyde (75-07-0,9002-91-9) → (3S,4R,5R)-3-[(R)-1-hydroxyethyl]-5-{(1R,2S,5R)-[2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one (1449306-99-3) + (3S,4R,5R)-3-[(S)-1-hydroxyethyl]-5-{(1R,2S,5R)-[2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one (1449307-00-9)

Guidance literature:

With trimethyl(benzyl)ammonium fluoride; In tetrahydrofuran; at -78 - -10 ℃; for 2.3h; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tet.2013.05.091

Reference yield:

C17H28O5 (1449307-33-8) → (3S,4R,5R)-3-[(S)-1-hydroxyethyl]-5-{(1R,2S,5R)-[2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one (1449307-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

2.1: trimethyl(benzyl)ammonium fluoride / tetrahydrofuran / 2.3 h / -78 - -10 °C / Molecular sieve; Inert atmosphere

With trimethyl(benzyl)ammonium fluoride; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/j.tet.2013.05.091

Reference yield:

C14H24O5 (1449307-34-9) → (3S,4R,5R)-3-[(S)-1-hydroxyethyl]-5-{(1R,2S,5R)-[2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one (1449307-00-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: boron trifluoride diethyl etherate / ethyl acetate / 8 h / 0 - 20 °C

2.1: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

3.1: trimethyl(benzyl)ammonium fluoride / tetrahydrofuran / 2.3 h / -78 - -10 °C / Molecular sieve; Inert atmosphere

With boron trifluoride diethyl etherate; trimethyl(benzyl)ammonium fluoride; lithium diisopropyl amide; In tetrahydrofuran; ethyl acetate;

DOI:10.1016/j.tet.2013.05.091

upstream raw materials:

C₁₇H₂₈O₅

(5R)-(L-menthyloxy)-2(5H)-furanone

C₁₄H₂₄O₅

(3R,4S,5R)-5-{(1R,2S,5R)-[2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-3-(trimethylsilyl)-4,5-dihydro-3H-furan-2-one

Downstream raw materials:

(4R,5R)-4-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one

(4S,5R)-2-[(S,3E,5E)-5,7-dimethyl-2-oxonona-3,5-dienyl]-4-[(R)-1-hydroxyethyl]-4,5-(isopropylidenedioxy)-3-phenylcyclopent-2-en-1-one

(2R,3S,4S)-3-benzoyl-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)pentanoic acid

(2R,3S)-3-[(S)-1-(tert-butyldimethylsiloxy)ethyl]-2,3-(isopropylidenedioxy)-4-oxo-4-phenylbutanal