82185-84-0

Upstream product

• 556-56-9 allyl iodid 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 106-95-6 allyl bromide 
• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 
• 3970-20-5 allyl chloromethyl ether 

Downstream Products

• 246162-52-7 6-O-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 

Relevant academic research and scientific papers

Allylation of sugar diols under phase transfer conditions using potassium carbonate as a base. Unexpected formation of cyclic carbonates

Allylation of sugar vic-diols (with a primary and secondary OH groups) under the phase transfer conditions (allyl bromide, K2CO3, 18-crown-6, toluene) afforded a mixture of both monosubstituted allyl ethers and small amounts of the di-allyl derivative. Interestingly, the cyclic carbonate was also isolated from the post reaction mixture. Its formation may be explained by reaction of the di-allyl carbonate, formed in situ under the reaction conditions, with the 1,2-diol. The structure of mono-allylated isomers can be easily assigned from the chemical shift (δc) of the CH2OR group (for R = H; All).

Elongation of the pentose chain at the terminal carbon atom with Grignard C1 reagents. A study of the homologation reaction

Derivatives of four stereoisomeric pentodialdo-1,4-furanoses were reacted with four Grignard C1 reagents: methoxymethyl-, allyloxymethyl-, benzyloxymethyl, and dimethylphenylsilylmethyl-magnesium chlorides. Derivatives of the expected stereoisomeric hexoses were accompanied in some cases by C-4 inverted products. The results have been discussed in terms of α- and β-chelated transition states. It has been found that the RX (X=O,Si) grouping of the Grignard reagent strongly influences the stereochemical outcome of the elongation reaction.

Glycosylation with 1,2-anhydromannofuranose benzyl ether as the glycosyl donor: A comparison between sugar pyranose and furanose acceptors for thelr primary hydroxy activity

Some 1→5 and 1→6 α-linked furano-disaccharide derivatives were synthesized using 1,2-anhydromannofiiranose as the glycosyl donor. Comparison of the glycosyl acceptors indicated that the activity of primary hydroxyl groups of glycofuranoses was much lower than that of glycopyranoses.