203447-96-5

Basic information

• Product Name: 5(R)-(Acetylamino)-2(S)-(5-bromo-1H-indol-3-yloxy)-6(R)-[2(R),3-dihydroxy-1(R)-methoxypropyl]-4(S)-methoxytetrahydro-2H-pyran-2-carboxylic acid
• CAS NO: 203447-96-5
• Molecular Formula: C₂₁H₂₇BrN₂O₉
• Molecular Weight: 531.36134
• Mol File: 203447-96-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5(R)-(Acetylamino)-2(S)-(5-bromo-1H-indol-3-yloxy)-6(R)-[2(R),3-dihydroxy-1(R)-methoxypropyl]-4(S)-methoxytetrahydro-2H-pyran-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5(R)-(Acetylamino)-2(S)-(5-bromo-1H-indol-3-yloxy)-6(R)-[2(R),3-dihydroxy-1(R)-methoxypropyl]-4(S)-methoxytetrahydro-2H-pyran-2-carboxylic acid(203447-96-5)
• EPA Substance Registry System: 5(R)-(Acetylamino)-2(S)-(5-bromo-1H-indol-3-yloxy)-6(R)-[2(R),3-dihydroxy-1(R)-methoxypropyl]-4(S)-methoxytetrahydro-2H-pyran-2-carboxylic acid(203447-96-5)

Safety Data

• Hazardous Substances Data: 203447-96-5(Hazardous Substances Data)

Upstream product

• 114165-30-9 1-acetyl-5-bromo-3-hydroxyindole 

Relevant articles and documents

Synthesis of bromoindolyl 4,7-di-O-methyl-Neu5Ac: Specificity toward influenza A and B viruses

N-Acetylneuraminic acid (Neu5Ac) was converted into the methyl ester methyl ketoside-8,9-epoxy derivative (8). Methylation of 8 followed by deprotection gave 4,7-di-O-methyl-Neu5Ac (10). Compound 10 was converted into the corresponding methyl ester-chloroacetate derivative, which was subsequently coupled to 5-bromo-indol-3-ol to give the chromogenic product (13). Deprotection of 13 gave 5-bromo-indol-3-yl 4,7-di-O-methyl-Neu5Ac (5). The product 5 was specifically cleaved by sialidase from either influenza A or influenza B virus to give an indigo-blue precipitate, but was not cleaved by several bacterial or viral sialidases tested. The properties of product 5 relative to a fluorescent substrate for sialidase were also documented. Copyright (C) 1999 Elsevier Science Ltd.