109923-13-9

Upstream product

• 109923-12-8 methyl 2,3-anhydro-4-O-benzyl-6-deoxy-α-D-allopyranoside 
• 74-89-5 methylamine 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 109923-10-6 methyl 4-O-benzyl-6-deoxy-6-iodo-2,3-di-O-p-tolylsulfonyl-α-D-glucopyranoside 
• 109923-09-3 methyl 4-O-benzyl-2,3-di-O-p-tolylsulfonyl-α-D-glucopyranoside 
• 109923-11-7 methyl 4-O-benzyl-6-deoxy-2,3-di-O-p-tolylsulfonyl-α-D-glucopyranoside 
• 6884-01-1 methyl 4,6-O-benzylidene-2,3-di-O-p-toluenesulphonyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

SYNTHESIS OF 3,6-DIDEOXY-3-(METHYLAMINO)HEXOSES FOR G.L.C.-M.S. IDENTIFICATION OF RHIZOBIUM LYPOSACCHARIDE COMPONENTS

A direct synthetic route from methyl α-D-glucopyranoside to 3,6-dideoxy-3-(methylamino)hexoses having the D-gluco, D-galacto, and D-manno configurations has been developed.Methyl α-D-glucoside was converted into the 4,6-O-benzylidene-2,3-di-O-tosyl derivative, which was then transformed into the 4-O-benzyl-6-deoxy 2,3-ditosylate (5) by successive reductive cleavage of the acetal ring, iodination, and reduction.The intermediate 5 was readily converted into the allo 2,3-epoxide, which yielded the pivotal intermediate methyl 4-O-benzyl-3,6-dideoxy-3-(methylamino)-α-D-glucopyranoside (7) by cleavage of the oxirane ring with methylamine.The amino compound 7 can be directly converted into the derivatized galacto and manno derivatives for mass-spectrometric identification by selective inversion at C-4 and C-2, respectively, followed by hydrolysis, reduction, and acetylation.