13965-63-4

Usage

Uses

Used in Pharmaceutical Industry:
(2R)-2-[(5alpha,18R)-3,6-dimethoxy-17-methyl-7,8-didehydro-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-18-yl]-4-phenylbutan-2-ol is used as a potential opioid or analgesic drug for its significant pharmacological activity. Its unique structure and stereochemistry may contribute to its efficacy in managing pain and potentially offering advantages over existing opioid medications.
Used in Research and Development:
In the field of medicinal chemistry and drug discovery, (2R)-2-[(5alpha,18R)-3,6-dimethoxy-17-methyl-7,8-didehydro-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-18-yl]-4-phenylbutan-2-ol serves as a valuable compound for studying the structure-activity relationships of opioids and analgesics. Its complex structure and potential pharmacological properties make it an interesting subject for further research to explore its therapeutic potential and optimize its properties for clinical use.

Synthetic route

thevinone (15358-22-2) + 2-phenyl-ethylmagnesium halide → (R)-2-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphinan-7α-yl)-4-phenyl-butan-2-ol (13965-63-4)

(R)-2-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphinan-7α-yl)-4-phenyl-butan-2-ol (13965-63-4) → (20R)-phenethyl-orvinol (14521-98-3)

Conditions	Yield
With potassium hydroxide In diethylene glycol Heating;

(R)-2-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphinan-7α-yl)-4-phenyl-butan-2-ol (13965-63-4) → (R)-2-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphin-15-en-7α-yl)-4-phenyl-butan-2-ol (36418-76-5)

Conditions	Yield
With hydrogen sulfide; mercury(II) oxide In acetic acid

(R)-2-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphinan-7α-yl)-4-phenyl-butan-2-ol (13965-63-4) → (2R,2'R)-4,4'-diphenyl-2,2'-[4,5α;4',5'α-diepoxy-3,6,3',6'-tetramethoxy-17,17'-methanediyl-bis-(6α,14α-etheno-morphinan-7α-yl)]-bis-butan-2-ol (16620-48-7, 16659-03-3)

Conditions	Yield
(i) diazenedicarbocylic acid diethyl ester, acetone, (ii) aq. H2O; Multistep reaction;

Upstream product

• 15358-22-2 thevinone 
• 3277-89-2 phenethylmagnesium bromide 

Downstream Products

• 14521-98-3 (20R)-(5α,7α)-4,5-epoxy-3-hydroxy-6-methoxy-α,17-dimethyl-α-(2-phenylethyl)-6,14-ethenomorphinan-7-methanol 
• 16620-48-7 (2R,2'R)-4,4'-diphenyl-2,2'-[4,5α;4',5'α-diepoxy-3,6,3',6'-tetramethoxy-17,17'-methanediyl-bis-(6α,14α-etheno-morphinan-7α-yl)]-bis-butan-2-ol 
• 36418-76-5 (R)-2-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphin-15-en-7α-yl)-4-phenyl-butan-2-ol 
• 14521-98-3 (20R)-phenethyl-orvinol 

Relevant academic research and scientific papers

Synthesis and evaluation of a full-agonist orvinol for PET-imaging of opioid receptors: [11C]PEO

Antagonist radiotracers have shown only a low sensitivity for detecting competition from high-efficacy agonists at opioid receptors (ORs) in vivo. We report that [11C]PEO binds with high affinity to μ and κ-opioid receptors, is a full agonist, and concentrates in brain regions of rats with a high density of the μ-OR after intravenous injection. Blocking studies with μ and κ-OR selective compounds demonstrated that the binding of [11C]PEO is saturable and selective to the μ-OR in rat brain.