4778-96-5

Usage

Uses

Used in Pharmaceutical Industry:
(5alpha,6alpha)-17-(2-phenylethyl)-4,5-epoxymorphinan-3,6,14-triol is used as a potential analgesic agent for the management of severe pain. Its classification under the morphinan class suggests that it may offer significant pain relief, similar to other opioids. However, the compound's exact efficacy and safety profile need to be thoroughly investigated to ensure its appropriate use in clinical settings.
Used in Research and Development:
(5alpha,6alpha)-17-(2-phenylethyl)-4,5-epoxymorphinan-3,6,14-triol serves as a subject of interest in scientific research, particularly in the fields of pharmacology and neuroscience. Its potential applications and impacts, as well as the mechanisms underlying its actions, are crucial areas of study. Understanding these aspects can contribute to the development of safer and more effective pain management strategies and may also provide insights into the broader opioid class of compounds.
Used in Drug Addiction and Dependence Studies:
Given the risks associated with tolerance, addiction, and physical dependence, (5alpha,6alpha)-17-(2-phenylethyl)-4,5-epoxymorphinan-3,6,14-triol is used as a research tool in addiction and dependence studies. Investigating its effects on the brain and the development of dependence can help in the design of strategies to mitigate these risks and improve the safety profile of opioid-based pain management therapies.

Synthetic route

4,5α-epoxy-3-methoxy-17-phenethyl-morphinane-6α,14-diol (6474-98-2) → 4,5α-epoxy-17-phenethyl-morphinane-3,6α,14-triol (4778-96-5)

Conditions	Yield
With boron tribromide In chloroform at 0 - 5℃; for 1h;	63%

beta-Noroxycodol (116499-16-2) → 4,5α-epoxy-17-phenethyl-morphinane-3,6α,14-triol (4778-96-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 56 percent / NaHCO3 / dimethylformamide / 20 h / 70 °C 2: 63 percent / BBr3 / CHCl3 / 1 h / 0 - 5 °C View Scheme

1-phenyl-2-bromoethane (103-63-9) + sodium salt of 4H-benz<1,4>oxazin-3-one → 4,5α-epoxy-17-phenethyl-morphinane-3,6α,14-triol (4778-96-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 56 percent / NaHCO3 / dimethylformamide / 20 h / 70 °C 2: 63 percent / BBr3 / CHCl3 / 1 h / 0 - 5 °C View Scheme

C22H24N2O6 (116388-83-1) → 4,5α-epoxy-17-phenethyl-morphinane-3,6α,14-triol (4778-96-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 10percent aq. HCl / 16 h / Heating 2: 56 percent / NaHCO3 / dimethylformamide / 20 h / 70 °C 3: 63 percent / BBr3 / CHCl3 / 1 h / 0 - 5 °C View Scheme

C24H27NO8 (142641-92-7) → 4,5α-epoxy-17-phenethyl-morphinane-3,6α,14-triol (4778-96-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: HCl gas / CH2Cl2 / 1 h 2: 56 percent / NaHCO3 / dimethylformamide / 20 h / 70 °C 3: 63 percent / BBr3 / CHCl3 / 1 h / 0 - 5 °C View Scheme

6α,14β-diacetoxy-4,5percenta-epoxy-3-methoxy-17-methyl-morphinan (67210-64-4) → 4,5α-epoxy-17-phenethyl-morphinane-3,6α,14-triol (4778-96-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / CHCl3 / 16 h / Heating 2: 10percent aq. HCl / 16 h / Heating 3: 56 percent / NaHCO3 / dimethylformamide / 20 h / 70 °C 4: 63 percent / BBr3 / CHCl3 / 1 h / 0 - 5 °C View Scheme
Multi-step reaction with 4 steps 1: 70 percent / NaHCO3 / 1,2-dichloro-ethane 2: HCl gas / CH2Cl2 / 1 h 3: 56 percent / NaHCO3 / dimethylformamide / 20 h / 70 °C 4: 63 percent / BBr3 / CHCl3 / 1 h / 0 - 5 °C View Scheme

Upstream product

• 6474-98-2 4,5α-epoxy-3-methoxy-17-phenethyl-morphinane-6α,14-diol 
• 67210-64-4 6α,14β-diacetoxy-4,5percenta-epoxy-3-methoxy-17-methyl-morphinan 
• 142641-92-7 C₂₄H₂₇NO₈ 
• 116388-83-1 C₂₂H₂₄N₂O₆ 
• 103-63-9 1-phenyl-2-bromoethane 
• 116499-16-2 beta-Noroxycodol 

Relevant academic research and scientific papers

Morphine Alkaloids, Part 114 A. Stereohomogeneous Synthesis of N-Demethyl-N-Substituted-14-Hydroxydihydromorphines

A new route for the stereohomogeneous synthesis of N-demethyl-N-substituted-14-hydroxydihydromorphines 2a-f has been elaborated, involving O-demethylation of the novel dihydrocodeine derivatives 6a-f, obtained upon alkylation of the hitherto unknown N-demethyl-14-hydroxydihydrocodeine (5). Keywords. 6α,14β-Diacetoxy-4,5α-epoxy-3-methoxy-17-methyl-morphinan, N-demethylation of; 3,6α,14β-Triacetoxy-17-alkyl-4,5α-epoxymorphinan, N-demethylation of; 17-Alkyl-4,5α-epoxy-6α,14β-dihydroxy-3-methoxymorphinan, O-demethylation of; 4,5α-Epoxy-6α,14β-dihydroxy-3-methoxymorphinan, N-alkylation of.