82185-84-0Relevant articles and documents
Allylation of sugar diols under phase transfer conditions using potassium carbonate as a base. Unexpected formation of cyclic carbonates
Jarosz,Szewczyk
, p. 1115 - 1122 (2007/10/03)
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
Stepowska, Halszka,Zamojski, Aleksander
, p. 5519 - 5538 (2007/10/03)
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.