155203-01-3

Basic information

• Product Name: (αS,5α,7α)-4,5-Epoxy-7-(1-hydroxy-1,2,2-triMethylpropyl)-3,6-diMethoxy-6,14-ethenoMorphinan-17-carbonitrile
• Synonyms: (αS,5α,7α)-4,5-Epoxy-7-(1-hydroxy-1,2,2-triMethylpropyl)-3,6-diMethoxy-6,14-ethenoMorphinan-17-carbonitrile
• CAS NO: 155203-01-3
• Molecular Formula: C27H34N2O4
• Molecular Weight: 450.57
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 155203-01-3.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (αS,5α,7α)-4,5-Epoxy-7-(1-hydroxy-1,2,2-triMethylpropyl)-3,6-diMethoxy-6,14-ethenoMorphinan-17-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (αS,5α,7α)-4,5-Epoxy-7-(1-hydroxy-1,2,2-triMethylpropyl)-3,6-diMethoxy-6,14-ethenoMorphinan-17-carbonitrile(155203-01-3)
• EPA Substance Registry System: (αS,5α,7α)-4,5-Epoxy-7-(1-hydroxy-1,2,2-triMethylpropyl)-3,6-diMethoxy-6,14-ethenoMorphinan-17-carbonitrile(155203-01-3)

Safety Data

• Hazardous Substances Data: 155203-01-3(Hazardous Substances Data)

Usage

Uses

(αS,5α,7α)-4,5-Epoxy-7-(1-hydroxy-1,2,2-trimethylpropyl)-3,6-dimethoxy-6,14-ethenomorphinan-17-carbonitrile is an intermediate in the synthesis of 18,19-Dehydrobuprenorphine (D229310), an analogue of Buprenorphine (B689570).

Upstream product

• 506-68-3 bromocyane 
• 13965-70-3 4,5α-epoxy-6α,14α-etheno-7α-(1-hydroxy-1,2,2-trimethylpropyl)-3,6β-dimethoxy-17-methylmorphinan 
• 115-37-7 thebaine 
• 15358-22-2 thevinone 

Downstream Products

• 52485-79-7 Buprenorphine 

Relevant articles and documents

Synthesis and pharmacological evaluation of 18,19-Dehydrobuprenorphine

18,19-Dehydrobuprenorphine (2) was prepared in five steps starting from thevinone (3) which is readily available from thebaine by Diels-Alder reaction. Grignard reaction with tert-BuMgBr afforded tert-butylthevinol (4) which was N-demethylated via N-cyano-tert-butylthevinol (5) using BrCN. Alkali treatment gave N-nor-tert-butylthevinol (6) which was alkylated with cyclopropylmethyl bromide to give N-cyclopropylmethyl-tert-butylthevinol (7), followed by ether cleavage with thiolate to yield 2. 18,19-Dehydrobuprenorphine displayed in opioid receptor binding studies very high affinity for μ receptors, while the affinity for κ and δ receptors was lower. In the tail-flick test in mice, compound (2) was 25 times more potent than morphine and ca. 2.5 times as potent as buprenorphine.