METHODS OF OBTAINING AMINOALKYLGLUCOSAMINIDPHOSPHATES AND DISACCHARIDE IMMUNOEFFECTORS AND THEIR INTERMEDIATE COMPOUNDS Russian patent published in 2008 - IPC C07H5/02 C07H9/02 C07H11/04 C07H13/04 C07H13/06 C07H15/04 

FIELD: chemistry.

SUBSTANCE: in method of obtaining compound aminoalkyl glucosaminide 4-phosphate of formula , X represents , Y represents -O- or NH-; R¹, R² and R³, each is independently selected from hydrogen and saturated and unsaturated (C₂-C₂₄) aliphatic acyl groups; R⁸ represents -H or -PO₃R¹¹R^11a, where R^11a and R^11a, each is independently -H or (C₁-C₄) aliphatic groups; R⁹ represents -H, -CH₃ or -PO₃R^13aR¹⁴, where R^13a and R¹⁴, each is independently selected from -H and (C₁-C₄) aliphatic groups, and where indices n, m, p, q each independently is a integer from 0 to 6 and r is independently integer from 2 to 10; R⁴ and R⁵ are independently selected from H and methyl; R⁶ and R⁷ are independently selected from H, OH, (C₁-C₄) oxyaliphatic groups -PO₃H₂, -OPO₃H₂, -SO₃H, -OSO₃H, -NR¹⁵R¹⁶, -SR¹⁵, -CN, -NO₂, -CHO, -CO₂R¹⁵, -CONR¹⁵R¹⁶, -PO₃R¹⁵R¹⁶, -OPO₃R¹⁵R¹⁶, -SO₃R¹⁵ and -OSO₃R¹⁵, where R¹⁵ and R¹⁶, each is independently selected from H and (C₁-C₄) aliphatic groups, where aliphatic groups are optionally substituted with aryl; and Z represents -O- or -S-; on condition that one of R⁸ and R⁹ represents phosphorus-containing group, but R⁸ and R⁹ cannot be simultaneously phosphorus-containing group, including: (a) selective 6-O- silylation of derivative of 2-amino-2-desoxy-β-D-glucopyranose of formula , where X represents O or S; and PG independently represent protecting group, which forms ester, ether or carbonate with oxygen atom of hydroxy group or which forms amide or carbamate with amino group nitrogen atom, respectively; by means of tri-substituted chlorosilane R_aR_bR_cSi-Cl, where R_a, R_b and R_c are independently selected from group, consisting of C₁-C₆alkyl C₃-C₆cycloalkyl and optionally substituted phenyl, in presence of tertiary amin, which gives 6-silylated derivative; (b) selective acylation of 4-OH position of obtained 6-O-silylated derivative with 6-3-alkanoyloxyalcanoic acid or hydroxyl-protected (R)-3-hydroxyalkanoic acid presence of a carbodiimide reagent and catalytic 4-dimethylaminopyridine or 4-pyrrolidinopyridine to give a 4-O-acylated derivative; (c) selectively deprotecting the nitrogen protecting groups, sequentially or simultaneously and N,N-diacylating the resulting diamine with (R)-3-alkanoyloxyalkanoic acid or a hydroxy-protected (R)-3-hydroxyalkanoic acid in presence of peptide condensation reagent; (d) introducing a protecting phosphate group at 3-position with a chlorophosphate or phosphoramidite reagent to give a phosphotriester; and (e) simultaneous or sequential deprotecting phosphate, silyl, and remaining protecting groups.

EFFECT: method improvement.

11 cl, 3 ex