5488-90-4

Upstream product

• 5111-12-6 1,2-O-isopropylidene-5-O-methyl-α-D-glucofuranurono-6,3-lactone 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 74-88-4 methyl iodide 
• 25577-41-7 3,6-di-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 2946-01-2 (3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate 
• 28642-58-2 O⁶-benzoyl-O¹,O²-isopropylidene-O³-(toluene-4-sulfonyl)-α-D-glucofuranose 
• 3067-56-9 D-glucurono-3,6-lactone acetonide 
• 186581-53-3 diazomethane 
• 253328-56-2 1,2-O-isopropylidene-α-D-gluco-/β-L-idofuranose 
• 3253-75-6 1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside 
• 14980-10-0 1,2-O-isopropylidene-5-O-methyl-3,6-di-O-acetyl-α-D-glucofuranose 

Downstream Products

• 108903-27-1 D-(1R)-O³-methyl-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-erythritol 
• 1071668-15-9 O⁵-methyl-D-arabino-[2]hexosulose-bis-phenylhydrazone 

Relevant academic research and scientific papers

MECHANISM OF METHYLATION OF NUCLEOSIDE SUGAR HYDROXYL GROUPS BY DIAZOMETHANE IN THE PRESENCE OF STANNOUS CHLORIDE

Diazomethane rapidly reacts with SnCl2 in methanol to give MeCl and Sn(OMe)2, both of which were isolated and identified.This reaction is the initial step in the apparent SnCl2*2H2O-catalysed methylation of nucleoside by diazomethane.The actual catalyst, Sn(OMe)2, readily reacts with Broensted acids, with exchange of ligands.For ribofuranosyl nucleusides, Sn2+ binds to site(s) having a labile proton, the effect being particulary predominant with 5- and 6-membered cyclic structures, with the tin ion co-ordinated to the ionised hydroxyl groups of the sugar moiety.These cyclic structures account for the high reactivity of the hydroxyl groups towards Me+, as in the complexes of ribofuranosyl nucleosides with Bu2SnO.A similar, if not identical, mechanism operates in the case of glucopyranosides.