33208-46-7

Upstream product

• 6167-32-4 1,6:3,4-dianhydro-2-O-tosyl-D-galactose 
• 100-39-0 benzyl bromide 
• 34147-05-2 1,6:2,3-dianhydro-β-D-gulopyranose 
• 23643-29-0 1,6-anhydro-4-O-(4-toluenesulfonyl)-β-D-glucopyranose 

Downstream Products

• 82742-17-4 1,6-anhydro-2-O-benzyl-4-C-cyano-4-deoxy-β-D-glucopyranose 
• 97119-82-9 1,6-Anhydro-2-O-benzyl-4-(cyclohexylamino)-4-desoxy-β-D-glucopyranose 
• 176389-14-3 (1S,2S,3S,4R,5R)-4-Benzyloxy-2-((1R,4R,5S,6S)-4,5,6-tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol 
• 213594-46-8 1,6-Anhydro-2-O-benzyl-4-benzylamino-4-deoxy-β-D-glucopyranose 
• 145240-53-5 1,6-Anhydro-4-azido-2-O-benzyl-4-deoxy-β-D-glucopyranose 
• 132016-21-8 1,6-anhydro-4-deoxy-4-<(1R,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-enyl>amino-β-D-glucose 
• 176389-15-4 (1S,2S,4R,5R,6R)-5-Benzyloxy-3-((1R,4R,5S,6S)-4,5,6-tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enyl)-7,9-dioxa-3-aza-tricyclo[4.2.1.0^2,4]nonane 
• 176389-16-5 (1S,2R,6S,7R,8R)-7-Benzyloxy-3-((1R,4R,5S,6S)-4,5,6-tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enyl)-5,9,11-trioxa-3-aza-tricyclo[6.2.1.0^2,6]undecan-4-one 
• 190791-74-3 Acetic acid (1S,2R,6S,7R,8R)-3-cyclohexyl-4-oxo-5,9,11-trioxa-3-aza-tricyclo[6.2.1.0^2,6]undec-7-yl ester 
• 190791-71-0 (1S,2R,6S,7R,8R)-7-Benzyloxy-3-cyclohexyl-5,9,11-trioxa-3-aza-tricyclo[6.2.1.0^2,6]undecan-4-one 

Relevant academic research and scientific papers

Synthesis of fluorinated thiodigalactoside analogues

In this work, we report the first synthesis of fluorinated thiodigalactoside analogues. We used tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the elaboration of two monofluorinated heterodimers, one difluorinated homodimer, and one difluorinated heterodimer. Moreover, we also present an alternative synthesis of 3-deoxy-3-fluorogalactose and 4-deoxy-4-fluorogalactose from a common precursor. Finally, this small set of more stable thiodigalactoside analogues could be interesting inhibitors of galactose-specific lectins.

Addressing the Structural Complexity of Fluorinated Glucose Analogues: Insight into Lipophilicities and Solvation Effects

In this work, we synthesized all mono-, di-, and trifluorinated glucopyranose analogues at positions C-2, C-3, C-4, and C-6. This systematic investigation allowed us to perform direct comparison of 19F resonances of fluorinated glucose analogues and also to determine their lipophilicities. Compounds with a fluorine atom at C-6 are usually the most hydrophilic, whereas those with vicinal polyfluorinated motifs are the most lipophilic. Finally, the solvation energies of fluorinated glucose analogues were assessed for the first time by using density functional theory. This method allowed the log P prediction of fluoroglucose analogues, which was comparable to the C log P values obtained from various web-based programs.

Synthesis and NMR spectra of 1,6-anhydro-2,3-dideoxy-2,3-epimino- and 1,6-anhydro-3,4-dideoxy-3,4-epimino-β-D-hexopyranoses

A complete series of 2,3-dideoxy-2,3-epimino-and 3,4-dideoxy-3,4-epimino-1,6-anhydro-β-D-hexopyranoses were prepared by lithium aluminum hydride reduction of the corresponding trans-azido tosylates or trans-azido epoxides of 1,6-anhydro-β-D-hexopyranoses. The structure of the epimino derivatives was confirmed by 1H and 13C NMR spectra.

Cyclitol Reactions, XII. - Enantioselective Synthesis of the Central Pseudodisaccharide Unit of α-Glycosidase Inhibitors of the Oligostatine Type

A pseudodisaccharide unit of the α-glycosidase inhibitors of the oligostatine type has been synthesized.At first a synthesis of the enantiomeric pure derivative of the branched amino inositol 26 has been developed.A linkage of 26 with the reactive epoxide