258349-81-4

Upstream product

• 504422-48-4 dodecyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 66854-07-7 dodecyl 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranoside 
• 112-53-8 1-dodecyl alcohol 
• 6801-92-9 n-dodecanyl β-D-galactopyranoside 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 

Downstream Products

• 504422-50-8 dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-56-4 dodecyl 2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-57-5 dodecyl 2,4,6-tri-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-51-9 dodecyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-54-2 dodecyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-52-0 dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-53-1 dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-arabino-hex-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-58-6 dodecyl 2,3,4,6-tetra-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

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.