3-O-trityl-6-O-desmethyl-buprenorphine

Base Information

• Chemical Name: 3-O-trityl-6-O-desmethyl-buprenorphine
• CAS No.: 1613511-98-0
• Molecular Formula: C₄₇H₅₃NO₄
• Molecular Weight: 695.942
• Mol file: 1613511-98-0.mol

Synonyms:

Chemical Property of 3-O-trityl-6-O-desmethyl-buprenorphine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-trityl-6-O-desmethyl-buprenorphine

There total 2 articles about 3-O-trityl-6-O-desmethyl-buprenorphine 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:

Buprenorphine (52485-79-7) → 3-O-trityl-6-O-desmethyl-buprenorphine (1613511-98-0)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / Reflux

2: triethylamine / dichloromethane

With lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm500503k

Reference yield:

trityl chloride (76-83-5) + 6-O-desmethyl-buprenorphine → 3-O-trityl-6-O-desmethyl-buprenorphine (1613511-98-0)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1021/jm500503k

Reference yield: 20.0%

2-fluoroethyl bromide (762-49-2) + 3-O-trityl-6-O-desmethyl-buprenorphine (1613511-98-0) → (5R,6R,7R,9R,13S,14S,20S)-(5α,7α)-17-cyclopropylmethyl-4,5-epoxy-18,19-dihydro-6-(2-fluoroethoxy)-3-triphenylmethoxy-α-(1,1-dimethylethyl)-α-methyl-6,14-ethenomorphinan-7-methanol (1613511-99-1) + C49H55NO4 (1613512-01-8)

Guidance literature:

3-O-trityl-6-O-desmethyl-buprenorphine; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.25h; Inert atmosphere;

2-fluoroethyl bromide; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jm500503k

upstream raw materials:

Buprenorphine

trityl chloride

Downstream raw materials:

(5R,6R,7R,9R,13S,14S,20S)-(5α,7α)-17-cyclopropylmethyl-4,5-epoxy-18,19-dihydro-6-(2-fluoroethoxy)-3-triphenylmethoxy-α-(1,1-dimethylethyl)-α-methyl-6,14-ethenomorphinan-7-methanol

C₄₉H₅₅NO₄

Refernces