β-D-Ribofuranose, 2-C-methyl-, 1,2,3,5-tetrabenzoate

White Powder

100 g (0.27 moles) of 3, 5-di O-benzoyl-2-C-methyl-D-ribofuranose synthesized in example 6 is added by stirring to 300 ml of acetonitrile, then 280 ml (2 moles) of triethylamine is added. 78.3 ml (0.67 moles) of benzoyl chloride is dripped at room temperature. At the end of the addition the mixture is warmed for 2 hours at 60 C., then an HPLC test is carried out.The reaction mixture is cooled to room temperature and 150 ml of water is added. The solid is filtered, washed with a mixture acetonitrile/water=2/1 and dried under vacuum up to constant weight. 109 g of product 1, 2, 3, 5-tetra-O-benzoyl-2-C-methyl-?-D-ribofuranose is obtained. Yield=70percent.The product 3, 5-di-O-benzoyl-2-C-methyl-D-ribofuranose (8.25 Kg22.2 moles) synthesized in example 23 is dissolved in 21 Kg of acetonitrile and then loaded in a 100 l reactor. 16.8 Kg (166.5 moles) of triethylamine is added and 9.8 Kg (69.7 moles) of benzoyl chloride is dripped; the temperature grows spontaneously. Then the mixture is heated at 60° C. for 4 hours. Thereafter the reaction is cooled at room temperature and 13.7 l of water is dripped. The mixture is cooled at 0° C. and is kept under stirring 1 hour. The solid is filtered and washed with 8 l of a mixture 2/1 acetonitrile/water cooled at 0° C. and then with 4.7 Kg of cold methyl alcohol.100 g (0.27 moles) of 3, 5-di O-BENZOYL-2-C-METHYL-D-RIBOFURANOSE synthesized in example 6 is added by stirring to 300 ml of acetonitrile, then 280 ml (2 moles) of triethylamine is added. 78.3 ml (0.67 moles) of benzoyl chloride is dripped at room temperature. At the end of the addition the mixture is warmed for 2 hours at 60 C, then an HPLC test is carried out. The reaction mixture is cooled to room temperature and 150 ml of water is added. The solid is filtered, washed with a mixture ACETONITRILE/WATER= 2/1 and dried under vacuum up to constant weight. 109 g of product 1, 2, 3, 5-tetra-O-benzoyl-2-C-methyl-?-D-ribofuranose is obtained. Yield = 70percent. 1H-NMR (CDC13, 300 MHz): 8 ppm 7.07 (1H, s, H-1) ; 5.96 (1H, d, H-3); 4.79 (1H, m, H- 4); 4.62 (2H, system AB, CH2-5). 13C-NMR (CDC13, 300 MHz): 6 ppm 97. 97 (C-1) ; 86.82 (C-4); 78.71 (C-3); 76.31 (C-2), 64.01 (C-5).A solution of the compound A2, 64 g of benzoyl chloride and 250 mL of dichloromethane were added to the reaction flask, and the mixture was cooled in an ice bath, stirred, and 48 g of triethylamine was slowly added dropwise. After the addition was completed, the reaction was stirred at 15 ° C for 3 hours. , washing with water, concentration, crystallization, to obtain compound A3, the total yield of step two and step three is 67.1percent

Molecular Weight:580.6
XLogP3:6.6
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:13
Exact Mass:580.17333247
Monoisotopic Mass:580.17333247
Topological Polar Surface Area:114
Heavy Atom Count:43
Complexity:957
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes