504422-28-0

Upstream product

• 504422-24-6 4,6-O-benzylidene-2,3-O-isopropylidene-5a-carba-β-D-glucopyranose 
• 504422-22-4 4,6-O-benzylidene-1,2-O-isopropylidene-5a-carba-β-D-glucopyranose 
• 504422-21-3 4,6-O-benzylidene-5a-carba-β-D-glucopyranose 
• 90695-20-8 (1S)-2-exo,3-endo-diacetoxy-5-endo-acetoxymethyl-7-oxabicyclo<2.2.1.>heptane 
• 90695-22-0 (1R)-(+)-(1,3,5/2,4)-2,3,4,5-tetrahydroxycyclohexane-1-methanol penta-acetate 
• 86117-82-0 (1R)-(+)-(1,3,5/2,4)-2,3,4,5-tetrahydroxycyclohexane-1-methanol 
• 111-83-1 1-bromo-octane 
• 17158-60-0 sodium octanolate 
• 108-24-7 acetic anhydride 
• 794535-78-7 (1R,3R,4S,5S,8R)-4-Benzyloxy-8-methoxymethoxy-3-octyloxy-6-oxa-bicyclo[3.2.1]octane 
• 504422-26-8 octyl 4,6-O-benzylidene-1,2-O-isopropylidene-5a-carba-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of 5a-carba-hexopyranoses and hexopyranosylamines, as well as 5a,5a′-dicarbadisaccharides, from 3,8-dioxatricyclo[4.2.1.0 2,4]nonan-9-ol: Glycosidase inhibitory activity of N-substituted 5a-carba-β-gluco- and β-galactopyranosylamines,

Since glycosidase and glycosyltransferase inhibitors, composed of carba-sugars, have recently attracted much attention, it is desirable to develop effective preparative routes for provision of new carba-sugar derivatives of potential biological interest.

Synthesis of an ether-linked alkyl 5a-carba-β-D-glucoside, a 5a-carba-β-D-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-D-glucoside, and an alkyl 5a′-carba-β-lactoside

For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-β-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine), in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-β-D-galactose residue into the 4-position of dodecyl β-D-glucopyranoside. A strong and specific inhibition of β-galactosidase (Ki 0.67 μM, bovine liver) was found for dodecyl 5a-carba-β-D-galactopyranoside.