6001-17-8

Upstream product

• 67-56-1 methanol 
• 154-17-6 D-2-deoxyglucose 
• 13145-22-7 methyl 2-deoxy-α-D-glucopyranoside 
• 29084-15-9 methyl 2-deoxy-β-D-arabino-hexopyranoside 
• 98103-44-7 methyl 2-deoxy-β-D-arabino-hexofuranoside 

Downstream Products

• 88756-98-3 m thyl 2-deoxy-6-O-p-tolylsulfonyl-α-D-arabino-hexofuranoside 
• 98050-06-7 methyl α-D-threo-pentodialdo-1,4-furanoside 
• 88757-03-3 9-(3,5-di-O-benzoyl-2,6-dideoxy-α,β-L-lyxo-hexofuranosil)hypoxanthine 
• 88757-01-1 methyl 3,5-di-O-benzoyl-2,6-dideoxy-β-L-lyxo-hexofuranoside 
• 88757-02-2 3,5-di-O-benzoyl-2,6-dideoxy-L-lyxo-hexofuranosil chloride 

Relevant academic research and scientific papers

Acid-catalyzed isomerization of methyl 2-deoxy-D-arabino-hexosides: Equilibria, kinetics and mechanism

Four isomers of methyl 2-deoxy-D-arabino-hexosides were isolated by HPLC as chromatographically homogeneous compounds. The rates of pyranoside isomerization (αp and βp) at 40°C and of furanoside isomerization (αf and βf) at 26°C were determined. A mechanism has been suggested for transformations taking place during isomerization of methyl 2-deoxy-D-arabino-hexosides in methanolic solution catalyzed with hydrogen chloride.

Synthesis of 2-deoxy-D-arabino-(6-13C)hexose.

2-Deoxy-D-arabino-[6-13C]hexose (10), to be used to test the stability of 2-deoxy-D-arabino-hexose 6-phosphate in brain tissue, was prepared. 2-Deoxy-D-arabino-hexose was labeled at C-6 because of the large difference in chemical shift between C-6 in the free sugar and C-6 in the 6-phosphate. The synthetic scheme resembled that used for the synthesis of D-[6-13C]glucose that involved the removal of C-6 from D-glucose followed by its replacement with 13C. The protected derivative methyl 2-deoxy-alpha-D-arabino-hexofuranoside was prepared, using trifluoroacetic acid in methanol. This was treated with periodate, which cleaves only between C-5 and C-6, to afford an aldehyde which reacted directly with K13CN to give a mixture of the D-arabino and L-xylo nitriles. The enriched nitriles were reduced with hydrogen in the presence of 5% Pd-carbon catalyst to a mixture of 6-aldehydo sugars. These were reduced with NaBH4 to a mixture of the two labeled methyl furanosides. Acid hydrolysis followed by ion-exchange chromatography on AG-50(Ca2+) resin at 65 degrees gave 10 in an overall yield of 16% from K13CN.