1426173-86-5

Basic information

• Product Name: C₂₅H₂₈⁽²⁾H₄F₃N₃O₄
• CAS NO: 1426173-86-5
• Molecular Weight: 499.51
• Mol File: 1426173-86-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: C₂₅H₂₈⁽²⁾H₄F₃N₃O₄(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₅H₂₈⁽²⁾H₄F₃N₃O₄(1426173-86-5)
• EPA Substance Registry System: C₂₅H₂₈⁽²⁾H₄F₃N₃O₄(1426173-86-5)

Safety Data

• Hazardous Substances Data: 1426173-86-5(Hazardous Substances Data)

Usage

Uses

Silodosin-d4 is an isotopic labelled form of Silodosin (S465000). Silodosin is an α1a-Adrenoceptor antagonist. It is used in treatment of benign prostatic hypertophy.

Upstream product

• 239463-85-5 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt 
• 239463-72-0 5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile 
• 160968-99-0 2-O-(2,2,2-trifluoroethyl)catechol 
• 90-05-1 2-methoxy-phenol 
• 1051374-58-3 (R)-1-(3-(benzyloxy)propyl)-5-(2-(2-(2-(2,2,2-trifluoro-1-d2-ethoxy)phenoxy)ethyl-d4-amino)propyl)indoline-7-carbonitrile 
• 1051374-64-1 1-(2-bromo-d4-ethoxy)-2-(2,2,2-d2-trifluoroethoxy)benzene 
• 1051374-63-0 2-(2,2,2-trifluoro-1-d2-ethoxy)phenol 
• 1051374-62-9 1-methoxy-2-(2,2,2-trifluoro-1-d2-ethoxy)benzene 
• 1051374-60-7 (R)-1-(3-hydroxypropyl)-5-(2-(2-(2-(2,2,2-trifluoro-1-d2-ethoxy)phenoxy)ethyl-d4-amino)propyl)indoline-7-carbonitrile 

Relevant articles and documents

Synthesis of silodosin glucuronide and its deuterated counterpart: Solving a problematic O-glycosylation of a nitrogen-containing molecule

We report here the first chemical synthesis of silodosin glucuronide, a metabolite of the α1A-adrenoceptor antagonist silodosin, and its deuterium-labeled counterpart. As a key synthetic step, the incorporation of a glucuronosyl unit onto silodosin invariably led to either an undesired orthoester or a complex mixture under an array of standard glycosylation conditions. This problematic O-glycosylation may be attributed to the presence of multiple basic groups that could neutralize the acidic activators, decrease the nucleophilicity of a hydroxy group via hydrogen bond or even facilitate acyl migration side reactions. After elaborate tuning of reaction conditions, success was eventually achieved by using perbenzoylated d-glucuronosyl N-phenyltrifluroacetimidate (PTFA) as donor in combination with a procedure of sequential addition of TMSOTf. This protocol is potentially general for the glycosylation of other nitrogen-containing small molecule drugs.