16713-89-6

Upstream product

• 50600-39-0 5-deoxy-5-iodo-1,2-O-isopropylidene-alpha-D-xylofuranose 
• 16713-88-5 1,2-O-isopropylidene-3-O-tosyl-α-D-xylopentofuranose 
• 29873-56-1 5-deoxy-5-iodo-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-xylofuranose 
• 98-59-9 p-toluenesulfonyl chloride 
• 4152-79-8 1,2-O-isopropylidene-5-methyl-5-deoxy-α-D-xylofuranose 

Downstream Products

• 68660-56-0 1,2-di-O-acetyl-5-deoxy-3-O-p-tolylsulfonyl-D-xylofuranose 
• 68660-57-1 methyl 5-deoxy-3-O-(p-toluenesulfonyl)-β-D-xylofuranoside 
• 16136-73-5 methyl 5-deoxy-3-O-(p-toluenesulfonyl)-α-D-xylofuranoside 
• 93215-29-3 methyl-2,5-didesoxy-2-C-methyl-3-O-benzyl-α-D-arabinofuranoside 
• 93215-32-8 3-O-benzyl-2,5-dideoxy-2-C-methyl-β-D-arabinofuranose 
• 93215-31-7 3-O-benzyl-2,5-dideoxy-2-C-methyl-α-D-arabinofuranose 

Relevant academic research and scientific papers

Enzymic hydrolysis of methyl 2,3-di-O-acetyl-5-deoxy-α and β-D-xylofuranosides - An active-site model of pig liver esterase

The regioselective enzymic hydrolysis of methyl 2,3-di-O-acetyl-5-deoxy-α-D-xylofuranoside (1) and methyl 2,3-di-O-acetyl-5-deoxy-β-D-xylofuranoside (2) in the presence of pig liver esterase (PLE) was studied by GLC. Diacetate 2 gave exclusively methyl 3-

Metal-Graphite Reagents in Carbohydrate Chemistry. 8. The Scope and Limitations of the Use of Zinc/Silver-Graphite in the Synthesis of Carbohydrate-Derived Substituted Hex-5-enals and Pent-4-enals

The compatibility of different organic functional groups with the use of the zinc/silver-graphite reagent was investigated, utilizing 23 6-bromo-6-deoxy- or 6-deoxy-6-iodohexopyranosides and 5-deoxy-5-iodopentofuranose derivatives.These compounds possessed O-acetyl, O-benzoyl, O-methyl-, or O-p-tolylsulfonyl, O-benzyl, O-methyl, O-isopropylidene, epoxy, acetamido deoxy, azido deoxy, chloro deoxy, and deoxy fluoro groups and included a mono and a dideoxy derivative.Reductive dealkoxyhalogenation of these compounds gave, in most instances, a single product, a hex-5- or pent-4-enal, which could be considered a precursor for carbocyclization reactions.Iodides reacted faster than bromides, and pyranose derivatives reacted faster and more cleanly than furanose derivatives.The kinetic or thermodynamic stability of the product enal was found to be structure-dependent.Reduction of the carbon-halogen bond was one of the few side reactions observed.A mechanism for the reductive ring cleavage is proposed.

SYNTHESIS OF 2,5-DIDEOXY-2-C-METHYL-D-ARABINOSE DERIVATIVES FROM METHYL 2,3-ANHYDRO-5-DEOXY-α-D-RIBOFURANOSIDE

Treatment of methyl 2,3-anhydro-5-deoxy-α-D-ribofuranoside with lithium dimethyl cuprate gave methyl 2,5-dideoxy-2-C-methyl-α-D-arabinofuranoside (54 percent) and methyl 3,5-dideoxy-3-C-methyl-α-D-xylofuranoside (10 percent).The former was converted into