34322-91-3

Upstream product

• 67-64-1 acetone 
• 6619-09-6 methyl 6-O-tosyl-α-D-glucopyranoside 
• 77-76-9 2,2-dimethoxy-propane 
• 26275-20-7 6-deoxy-1,2-O-isopropylidene-6-(4'-methylbenzene)sulfonyloxy-D-glucofuranose 
• 98-59-9 p-toluenesulfonyl chloride 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 116-11-0 2-Methoxypropene 
• 72733-20-1 (1,2;5,6-Di-O-isopropyliden-α-D-glucofuranos-3-yloxy)phosphonium-p-toluolsulfonat 
• 28528-94-1 1,2;3,5-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 20847-06-7 O⁶-(toluene-4-sulfonyl)-D-glucose 
• 32785-99-2 6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-glucofuranoside 
• 79940-58-2 6-deoxy-6-C-(diphenylphosphinyl)-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose 
• 70156-10-4 6-deoxy-6-C-(diphenylphosphino)-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose 

Relevant academic research and scientific papers

Carbohydrate biguanides as potential hypoglycemic agents

A series of monosaccharides containing a biguanide functionality was prepared and evaluated for hypoglycemic activity. Among the analogues prepared were those involving D-glucose substituted on the 6- or 1- position (19 and 24), D-galactose substituted on

Synthesis of N-alkoxytrihydroxypiperidine analogs of allopyranose

Tandem reductive cyclization of O-alkyl oximes provides an efficient method for the preparation of N-alkoxytrihydroxypiperidine analogs of allopyranose as potential glycosidase inhibitors.

Synthesis and Reactions of 3-O-Phosphoniogluco- and Allofuranoses

Starting from the bicyclic gluco- (3,5,7, and 9) and allofuranoses 11 the isolable 3-O-phosphoniocarbohydrates (4,6,8,10, and 12) were synthesized by reaction with triphenylphosphane (1), diethyl azodicarboxylate (2), and alkylating or acylating agents.On heating, the various allo configurated salts 12 are converted into the corresponding at C-3 epimeric gluco configurated substitution products offering a wide range of flexibility.The reactions of the gluco configurated salts depend strongly on the type of nucleophile to be introduced and from neighboring groups in t he carbohydrate skeleton.The iodide 4a and the azide 4g react by substitution forming the allo derivatives 15.In contrast, bromide, chloride, and sulfonate as gegen-ions mainly cause rearrangement of the 5,6-isopropylidene bridge or opening of the 5,6-anhydro structure.

Use of Ferric Chloride in Carbohydrate Reactions: Part III-Reaction of Methyl Glycosides and Methyl 6-O-Tosyl Glycosides with Ferric Chloride-Acetone

Ferric chloride-acetone has been used for the preparation of O-isopropylidene derivates of methyl glycosides and methyl 6-O-tosyl glycosides.Using this reagent 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, methyl 4,6-O-isopropylidene-α-D-glucopyranoside, methyl 2,3-O-isopropylidene-α-D-galactopyranoside, methyl 4,6-O-isopropylidene-α-D-galactopyranoside, 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose,1,2:3,5-di-O-isopropylidene-6-O-tosyl-α-D-glucofuranose, 1,2:3,4-di-O-isopropylidene-6-O-tosyl-α-D-galactopyranose and methyl 3,4-O-isopropylidene-6-O-tosyl-α-D-galactopyranoside have been prepared.Inhibition by tosyl group in the hydrolysis of the glycosidic function has been rationalised.