111833-94-4

Upstream product

• 22893-69-2 Methyl (methyl-3-deoxy-α-D-manno-oct-2-ulopyranosid)onate 
• 111833-99-9 methyl (methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosid)onate 
• 100-39-0 benzyl bromide 
• 111833-93-3 (2R,4R,5R,6S)-6-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-4,5-dihydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 73650-00-7 methyl 4,5,7,8-tetra-O-acetyl-3-deoxyl-alpha-D-manno-2-octulopyranosonate 
• 118499-49-3 benzyl (methyl 3-deoxy-7,8-O-isopropylidene-α-D-manno-2-octulopyranosid)onate 
• 111833-93-3 methyl (methyl 3-deoxy-7,8-isopropylidene-α-D-manno-2-octulopyranosid)onate 
• 118499-48-2 benzyl (methyl 3-deoxy-α-D-manno-2-octulopyranosid)onate 

Downstream Products

• 111834-02-7 methyl-4,8-di-O-benzyl-3-deoxy-α-D-manno-2-octulopyranosidino-1,5-lactone 
• 111833-95-5 (1R,4R,6R,7R)-7-Benzyloxy-6-(1,2-dihydroxy-ethyl)-4-methoxy-2,5-dioxa-bicyclo[2.2.2]octan-3-one 
• 133634-98-7 methyl (methyl 3-deoxy-7,8-O-isopropylidene-5-O-methyl-α-D-manno-oct-2-ulopyranosid)onate 4-(diphenylphosphate) 
• 133635-12-8 methyl (methyl 3-deoxy-5,7,8-tri-O-methyl-α-D-manno-oct-2-ulopyranosid)onate 4-(diphenyl phosphate) 
• 133635-08-2 methyl (methyl 4-O-benzoyl-3-deoxy-7,8-O-isopropylidene-5-O-methyl-α-D-manno-oct-2-ulopyranosid)onate 
• 133635-10-6 methyl (methyl 4-O-benzoyl-3-deoxy-5,7,8-tri-O-methyl-α-D-manno-oct-2-ulopyranosid)onate 
• 133634-97-6 methyl (methyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-5-O-methyl-α-D-manno-oct-2-ulopyranosid)onate 
• 133635-09-3 methyl (methyl 4-O-benzoyl-3-deoxy-5-O-methyl-α-D-manno-oct-2-ulopyranosid)onate 
• 114729-36-1 (2R,4R,5R,6S)-4-Benzyloxy-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

SYNTHESIS OF 1,5-LACTONES OF 3-DEOXY-D-manno-2-OCTULOPYRANOSONIC ACID ( KDO)

An unambigous synthesis of methyl 3-deoxy-α-D-manno-2-octulopyranosidono-1,5-lactone from methyl (methyl 3-deoxy-α-D-manno-octulopyranosid)onate via the 7,8-O-isopropylidene derivative is described.Treatment of the 4,5-stannylene derivative of this acetal with benzyl bromide gave the 1,5-lactone from which the protecting groups were removed.The acetylated 1,5-lactone was produced by acetylation of ammonium 3-deoxy-D-manno-2-octulosonate or treatment of the pyridinium salt with dicyclohexylcarbodi-imide and acetylation.No lactone was produced when only HO-7 was unsubstituted.When treated with an excess of 2-methoxypropene, methyl (methyl 3-deoxy-α-D-manno-2-octulopyranosid)onate afforded the 4,5:7,8-di-O-isopropylidene derivative, from which the 7,8-acetal group could be removed selectively.

FORMATION OF 1,5-LACTONES FROM 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID DERIVATIVES.

Acylation of ammonium 3-deoxy-α-D-manno-2-octulopyranosonate (1a) leads to the formation of peracetylated 3-deoxy-α-D-manno-2-octulopyranosono-1,5-lactones (3a,b).The proposed structures were confirmed by independent syntheses.The 1,7-lactone was not formed even when only OH-7 was available for lactonisation.