94801-02-2

Usage

Chemical Properties

White to Off-White Solid

Upstream product

• 94801-01-1 5-azido-5-deoxy-1,2-O-isopropylidene-β-D-fructopyranose 
• 53821-66-2 Acetic acid (8S,9S,10S)-9-acetoxy-2,2-dimethyl-8-(toluene-4-sulfonyloxy)-1,3,6-trioxa-spiro[4.5]dec-10-yl ester 
• 94801-00-0 Acetic acid (8R,9R,10S)-9-acetoxy-8-azido-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]dec-10-yl ester 
• 99648-59-6 3,4-di-O-benzoyl-1,2-O-isopropylidene-β-D-fructopyranose 
• 25018-67-1 1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose 
• 94801-01-1 5-azido-5-deoxy-1,2-O-isopropylidene-β-D-fructopyranose 
• 368452-21-5 5-azideo-3,4-di-O-benzoyl-5-deoxy-1,2-O-isopropylidene-β-L-sorbopyranose 
• 368452-03-3 3,4-di-O-benzoyl-5-deoxy-5-iodo-1,2-O-isopropylidene-β-L-sorbopyranose 
• 76573-34-7 (-)-3-deoxy-1,2:4,5-di-O-isopropylidene-β-D-fructofuranos-3-yl benzoate 
• 99648-49-4 3-O-benzoyl-1,2-O-isopropylidene-β-D-fructopyranose 

Downstream Products

• 59920-31-9 2,5-dideoxy-2,5-imino-D-mannitol 
• 697288-29-2 (2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carbothioic acid phenylamide 
• 198691-31-5 (2R,3R,4R)-2,5-Bis-hydroxymethyl-3,4-dihydro-2H-pyrrole-3,4-diol 

Relevant academic research and scientific papers

Nickel(II)-catalysed transformations of 5-azido-5-deoxy-D-glucofuranose and of 5-azido-5-deoxy-L-idofuranose

Nickel(II) catalysed isomerisation reactions of C-5 modified derivatives of D-glucose as well as L-idose were investigated. 5-Azido-5-deoxy-D-glucofuranose was successfully isomerised into the corresponding D-manno epimer in good yields. Contrasting this result, in the case of the 5-modified L-idofuranose probed, no evidence for successful epimerisation at C-2 could be found. However, this sugar was quantitatively rearranged into the corresponding L-sorbopyranose. Upon extended reaction periods, the latter underwent degradation to give the coresponding 4-modified methyl L-xylonate.

Pseudoamide-Type Pyrrolidine and Pyrrolizidine Glycomimetics and Their Inhibitory Activities against Glycosidases

Coupling reaction of (2R,3R,4R,5R)-2,5-hydroxy-methyl-3,4-dihydroxypyrrolidine (DMDP) with isothiocyanates afforded the corresponding thiourea adducts, which were transformed into isourea-type bicyclic oxapyrrolizidine glycomimetics by mercury(II) oxide-assisted intramolecular sulfur displacement. Cyclic carbamate and thiocarbamate analogues were also prepared by direct carbonylation or thiocarbonylation of DMDP. Evaluation of the glycosidase inhibitory properties demonstrated that remarkable specificities in enzyme inhibition can be achieved upon modifications on the pseudoaglyconic side chain and on the nature of the sp2-hybridized endocyclic ring nitrogen.

2,5-Dideoxy-2,5-imino-D-mannitol and -D-glucitol. Two-step bio-organic syntheses from 5-azido-5-deoxy-D-glucofuranose and -L-idofuranose; evaluation as glucosidase inhibitors and application in affinity purification and characterisation of invertase from yeast

Glucose isomerase (EC 5.3.1.5) catalyzes the quantitative isomerisation of 5-azido-5-deoxy-D-gluco- (7) and -L-idofuranose (9), respectively, into the corresponding ketoses, 5-azido-5-deoxy-D-fructopyranose (8) and -L-sorbopyranose (10), respectively. Upon catalytic hydrogenation over palladium-on-charcoal, the fructose derivative 8 gives the natural product and the efficient glycosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol (4), while the sorbose derivative 10 affords 2,5-dideoxy-2,5-imino-D-glucitol (5). This represents a preparatively very simple and efficient two-step synthesis of these biologically active compounds. Both are strong inhibitors of α- and β-glucosidases from various sources, the D-manno-isomer 4 being distinctly more active. Because of its structural relationship with β-D-fructofuranose, compound 4 is also a vary good inhibitor of invertase from yeast and, as such, was for the first time employed, after immobilized and aminohexyl-sepharose, for the purification of this enzyme. Glucose isomerase (EC 5.3.1.5) catalyses the quantitative isomerization of 5-azido-5-deoxy-D-gluco (7) and -L-idofuranose (9), respectively, into the corresponding ketoses, 5-azido-5-deoxy-D-fructopyranose (8) and -L-sorbopyranose (10) respectively. Upon catalytic hydrogenation over palladium on 2,5-dideoxy-2,5-imino-D-mannitol (4), while the sorbose derivative 10 affords 2,5-dideoxy-2,5-imino-D-glucitol (5). This represents a preparatively very simple and efficient two-step synthesis of these biologically active compounds. Both are strong inhibitors of α- and β-glucosidases from various sources, the D-manno-isomer 4 being distinctly more active. Because of its structural relationship with β-D-fructofuranose, compound 4 is also a very good inhibitor of invertase from yeast and, as such, was for the first time employed, after immobilization on aminohexyl-sepharose, for the purification of this enzyme.

A novel synthetic application of glucose isomerase: Quantitative conversion of D-glucose and L-idofuranose, derivatives modified at position five into the corresponding D-fructo- and L-sorbopyranoses

Glucose isomerase (B.C. 5.3.1.5) quantitatively converts a wide range of D-glucose as well as L-idose derivatives modified at position five, such as 5-O-benzyl-, 5-azido-5-deoxy-, 5-deoxy-5-fluoro analogues into the corresponding 2-ketosugars. The reactio