119005-61-7

Upstream product

• 67-56-1 methanol 
• 119005-63-9 methyl onate 
• 119005-64-0 methyl onate 
• 211934-99-5 2,6-anhydro-4,5,7-tri-O-benzyl-1-(propane-1,3-diyl-dithioacetal)-1,3-dideoxy-D-arabino-hept-1-enitol 
• 79999-46-5 (4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 119005-70-8 Methyl 3-deoxy-2-phenylsulphonyl-4,5,7-tri-O-benzyl-D-arabino-heptulosonate 
• 119005-72-0 methyl <4,5,7-tri-O-benzyl-2,3-dideoxy-α-D-arabino-2-heptulopyranosid>onate 
• 119005-63-9 methyl onate 

Downstream Products

• 2880-95-7 methyl (methyl 3-deoxy-α-D-arabino-2-heptulopyranosid)onate 
• 120852-00-8 methyl 4,5,7-tri-O-benzyl-2-deoxy-D-arabino-2-heptulopyranosidonic acid 

Relevant academic research and scientific papers

Synthetic routes to methyl 3-deoxy-aldulosonic acid methyl esters and their 2-deoxy isomers based on the Horner-Emmons and Peterson reaction of sugar lactones

The two reagents: 2-trimethylsilyl- and 2-[bis(2,2,2- trifluoroethoxy)phosphoryl]-1,3-dithianes were engaged in the construction of appropriate ketene thioacetals from the isomeric 2-deoxy-hexono-1,5-lactones via Horner-Emmons or Peterson reaction. A comparison of the results shows that the second reagent is more promising, as it forms the desired ketene thioacetals as sole products. The latter were directly transformed stereoselectively into the title α ulosonates in an oxidative hydrolysis reaction, using NBS/MeOH in CH2Cl2. A construction of the methyl 2-deoxy- ulosonates involved a preceding hydrogenation of the double bond by LiBH4- TMSCl species, and subsequent hydrolysis with NBS in aqueous THF medium.

The first synthesis of the ketene dithioacetals from sugar lactones: A convenient access to 3-ulosonic acids

Isomeric 2-deoxy aldonolactones undergo Horner-Emmons reactions with 2- [bis(2,2,2-trifluoroethoxy)phosphoryl]1,3-dithiane, to give the corresponding ketene dithioacetals, which are the key intermediates in the synthesis of 3- deoxy-2-keto-aldonic acids.