6087-42-9

Upstream product

• 108-24-7 acetic anhydride 
• 3971-45-7 methyl 2-deoxy-α-D-galactopyranoside 
• 67-56-1 methanol 
• 4098-06-0 triacetyl-D-galactal 
• 53008-81-4 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-taloside 
• 245730-35-2 (2R,3S,4S,5S,6R)-6-(acetoxymethyl)-3-iodotetrahydro-2H-pyran-2,4,5-triyl triacetate 
• 1949-89-9 2-deoxy-D-galactose 
• 4163-60-4 β-D-galactose peracetate 

Relevant academic research and scientific papers

Practical synthesis of 2-deoxy sugars via metal free deiodination reactions

2-Deoxy-glycosides, in which the C-2 hydroxyl group is replaced with a hydrogen atom, are important motifs in numerous bioactive natural products and pharmaceutical molecules. Herein, an improved dilauroyl peroxide-mediated radical deiodination reaction b

TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.

Ferrier rearrangement and 2-deoxy sugar synthesis from d-glycals mediated by layered α-zirconium sulfophenylphosphonate-methanphosphonate as heterogeneous catalyst

Layered α-zirconium sulfophenylphosphonate-methanphosphonate is a solid acid catalyst that catalyzes Ferrier rearrangement from d-glycals and alcoholic nucleophiles under mild reaction conditions in short time and good yields. Notably, the combination of α-zirconium sulfophenylphosphonate- methanphosphonate and lithium bromide change the regioselectivity of this process affording 2-deoxy sugars in good yields. Graphical Abstract: [Figure not available: see fulltext.]

A new aspect of the reactivity of sodium dithionite provides a facile route to 2-deoxy-α-glycosides

Sodium dithionite, which is known to cause dehalogenation of α-halo carbonyl compounds, also induces dehalogenation of protected 2-iodo-2-deoxyglycosides. Combined with the well-known iodonium-mediated haloalkoxylation, this reaction provides an easy, mild and highly stereoselective route for preparation of 2-deoxy-α-glycosides from glycals.

The use of tri-O-acetyl-D-glucal and -D-galactal in the synthesis of 3-acetamido-2,3-dideoxyhexopyranoses and -hexopyranosides.

Addition of hydrazoic acid to alpha,beta-unsaturated aldehydes derived from tri-O-acetyl-D-glucal and -D-galactal gave 3-azido-2,3-dideoxyhexopyranoses. These were converted into 1,4,6-tri-O-acetyl-3-azido-2,3-dideoxyhexopyranoses as well as methyl and ethyl glycosides. Hydrogenation of the proamine group in 3-azido-2,3-dideoxy derivatives provided different 3-amino and 3-acetamido sugars. The configuration and conformation of all products were established on the basis of the 1H and 13 C NMR, IR and polarimetric data.