50256-48-9Relevant articles and documents
REACTION DE TRANSACETALISATION PAR LE DIMETHOXYMETHANE SYNTHESE DE O-METHYLENEACETAL DE DERIVES DU D(+)GLUCOSE
Nouguier, Robert,Gras, Jean-Louis
, p. 3423 - 3428 (1989)
The acid catalyzed and LiBr assisted transacetalization from dimethoxymethane applied to α and β glucosides allows the selective methylenation of the -4 and -6 hydroxyl functions.The α anomer leads to the compound 4 , but under the same conditions, the β anomer leads to a mixture of the methylene acetal protected carbohydrates 4 and 5.Glucose, under our transacetalization conditions, affords, after in-situ O-glycosidation and protection, the same compounds 4 and 5.The classical methylenation using formol/HCl with glucose and glucosides, does not lead to the expected products but to the same glucofuranoside compound 6 which results from a O-demethylation of the glucoside.
Synthesis of methylene acetals in the D-glucose, D-galactose, D-mannose, and D-fructose series by an improved transacetalation reaction from dimethoxymethane
Nouguier,Mignon,Gras
, p. 339 - 345 (2007/10/03)
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