84207-47-6

Upstream product

• 6167-32-4 1,6:3,4-dianhydro-2-O-tosyl-D-galactose 
• 64-19-7 acetic acid 
• 492-61-5 β-D-glucose 
• 498-07-7 levoglucosan 
• 93173-18-3 1,6-anhydro-4-O-acetyl-β-D-glucopyranose 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 84207-51-2 Acetic acid (1R,2R,3S,4R,5R)-3,4-bis-(toluene-4-sulfonyloxy)-6,8-dioxa-bicyclo[3.2.1]oct-2-yl ester 
• 26423-99-4 1,6:3,4-dianhydro-2-O-p-toluenesulfonyl-β-D-allopyranose 

Relevant academic research and scientific papers

Method for synthesizing intermediate of fondaparinux sodium

The invention discloses a method for synthesizing an intermediate of fondaparinux sodium represented by a formula 1. The method comprises the step of subjecting a compound represented by a formula 2 and benzaldehyde, which serve as reaction raw materials, to acetal protective reaction and diacetyl removing reaction in an organic solvent in the presence of mixed acid, thereby obtaining the intermediate of fondaparinux sodium represented by the formula 1 in one step, wherein the mixed acid is prepared from concentrated sulfuric acid and para-toluenesulfonic acid which are in the mass ratio of 1to (0.1 to 5), the concentrated sulfuric acid is a sulfuric acid aqueous solution with the mass fraction of 70% to 98%, the organic solvent contains toluene, of which the volume accounts for 5% to 15%that of the organic solvent; a volume ratio of water to the organic solvent in an initial reaction system is controlled to (0.005 to 0.04) to 1. The method has the advantages of being high in conversion ratio, high in reaction rate, simple in operation and applicable to large-scale production. The formula 1 and formula 2 are shown in the description.

PREPARATION OF 1,6:3,4-DIANHYDRO-β-D-ALTROPYRANOSE AS STARTING SUBSTANCE FOR THE SYNTHESIS OF 3-SUBSTITUTED D-MANNOSE DERIVATIVES

Acetolysis of 1,6:3,4-dianhydro-2-O-p-toluenesulfonyl-β-D-galactopyranose (I) gave 3,4-di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose (II) which was converted with sodium methoxide to 1,6:3,4-dianhydro-β-D-altropyranose (X).The 1,6-anhydride bond in diacetate II was cleaved with acetic anhydride or hydrogen bromide in acetic acid under formation of a mixture of anomeric tetraacetates of 2-O-p-toluenesulfonyl-D-glucopyranose or the corresponding acetates of α-D-glucopyranosyl bromide XIII and its 6-bromo-6-deoxy derivative XIV.