189143-93-9

Basic information

• Product Name: (2R,3R,4R,5R,6R)-5-Acetoxy-4-benzoylamino-3-bromo-2-methoxy-6-((1R,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• Synonyms: (2R,3R,4R,5R,6R)-5-Acetoxy-4-benzoylamino-3-bromo-2-methoxy-6-((1R,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS NO: 189143-93-9
• Molecular Weight: 646.443
• Mol File: 189143-93-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R,5R,6R)-5-Acetoxy-4-benzoylamino-3-bromo-2-methoxy-6-((1R,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R,5R,6R)-5-Acetoxy-4-benzoylamino-3-bromo-2-methoxy-6-((1R,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester(189143-93-9)
• EPA Substance Registry System: (2R,3R,4R,5R,6R)-5-Acetoxy-4-benzoylamino-3-bromo-2-methoxy-6-((1R,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester(189143-93-9)

Safety Data

• Hazardous Substances Data: 189143-93-9(Hazardous Substances Data)

Upstream product

• 100-47-0 benzonitrile 
• 123843-50-5 methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosid)onate 
• 173467-22-6 methyl 5,7,8,9-tetra-O-acetyl-2,6-anhydro-4-benzoylamino-3,4-dideoxy-D-glycero-D-galacto-non-2-enonate 
• 67-56-1 methanol 

Relevant articles and documents

Syntheses of sialic acid analogues with acylamino groups at C-4 (N-acyl regioisomers of sialic acids)

Methyl 5,7,8,9-tetra-O-acetyl-4-acylamino-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto and D-talo-non-2-enonates were synthesized from the reaction of the peracetate of Kdn methyl ester with several nitriles in the presence of a Lewis acid. Treatment of these 2,4-dideoxy-4-acylamino-Kdn methyl esters with N-bromosuccinimide in methanol gave methyl (methyl 5,7,8,9-tetra-O-acetyl-4-acylamino-3-bromo-3,4-dideoxy-D- erythro-α-L-manno-non-2-ulopyranosid)onates (16, 18, and 20) and oxazine-type derivatives, 2-alkyl-(methyl 5,7,8,9-tetra-O-acetyl-3 -bromo-3,4-dideoxy-D-erythro-α-L-manno-non-2- ulopyranosonate)-5,6-dihydro-4H-1.3-oxazine (29, 30, and 31). Debromination of 16, 18, and 20 with Bu3SnH/AIBN in toluene gave methyl (methyl 5,7,8,9-tetra-O-acetyl-4-acylamino-3,4-dideoxy-β-D-glycero-D-galacto -nonulopyranosid)onate (23, 24, and 25), whereas hydrolysis with HOAc and subsequent debromination with Bu3SnH/AIBN in toluene of 32 and 33 gave methyl 5,7,8,9-tetra-O-acetyl-4-acylamino-3,4-dideoxy-β-D-glycero-D-talo-2 -nonulopyranosonate (35 and 36) in the final step of the synthesis.