102043-71-0

Basic information

• Product Name: n-dodecanyl β-D-galactopyranoside
• CAS NO: 102043-71-0
• Molecular Weight: 348.48
• Mol File: 102043-71-0.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: n-dodecanyl β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: n-dodecanyl β-D-galactopyranoside(102043-71-0)
• EPA Substance Registry System: n-dodecanyl β-D-galactopyranoside(102043-71-0)

Safety Data

• Hazardous Substances Data: 102043-71-0(Hazardous Substances Data)

Upstream product

• 440652-81-3 isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 70191-05-8 2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 112-53-8 1-dodecyl alcohol 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 66854-07-7 dodecyl 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranoside 
• 1427214-08-1 dodecyl 4,6-O-benzylidene-β-D-galactopyrnoside 
• 25878-60-8 D-galactose pentaacetate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 4291-68-3 (2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran 
• 4163-60-4 β-D-galactose peracetate 

Downstream Products

• 263247-09-2 dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-β-D-galactopyranoside 
• 263247-10-5 dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside 
• 263247-08-1 dodecyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-β-D-galactopyranoside 
• 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 
• 504422-50-8 dodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-α-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-52-0 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 
• 258349-81-4 dodecyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 504422-48-4 dodecyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 

Relevant articles and documents

Antimicrobial and cytotoxic activity of (thio)alkyl hexopyranosides, nonionic glycolipid mimetics

A series of 19 synthetic alkyl and thioalkyl glycosides derived from D-mannose, D-glucose and D-galactose and having C10–C16 aglycone were investigated for cytotoxic activity against 7 human cancer and 2 non-tumor cell lines as well as for antimicrobial potential on 12 bacterial and yeast strains. The most potent compounds were found to be tetradecyl and hexadecyl β-D-galactopyranosides (18, 19), which showed the best cytotoxicity and therapeutic index against CCRF-CEM cancer cell line. Similar cytotoxic activity showed hexadecyl α-D-mannopyranoside (5) but it also inhibited non-tumor cell lines. Because these two galactosides (18, 19) were inactive against all tested bacteria and yeast strains, they could be a target-specific for eukaryotic cells. On the other hand, β-D-glucopyranosides with tetradecyl (11) and hexadecyl (12) aglycone inhibited only Gram-positive bacterial strain Enterococcus faecalis. The studied glycosides induce changes in the lipid bilayer thickness and lateral phase separation at high concentration, as derived from SAXS experiments on POPC model membranes. In general, glucosides and galactosides exhibit more specific properties. Those with longer aglycone show high cytotoxicity and therefore, they are more promising candidates for cancer cell line targeted inhibition.

Effect of anomeric linkage on the sialylation of glycosides by cells

The synthesis of sialylated glycosides using saccharide primers and cells was investigated. α·and β·Saccharide primers were chemically synthesized and introduced into B16 melanoma cells to prime oligosaccharide synthesis. Incorporation of α- and β-dodecyl lactosides into B16 cells resulted in the sialylation of the galactose residue to give GM3-type oligosaccharides. The β-dodecyl galactoside primer was sialylated but the α-dodecyl galactoside primer was not. Both the α- and β-dodecyl glucoside primers were not elongated. In the glycosylation of primers by cells, this research confirmed that sialyl transferases tolerate acceptor modifications and are permissive to primer elongation regardless of the α- or β-linkage to the aglycon unit. However, the presence of the terminal galactose residue that is β-linked to the adjacent saccharide or aglycon unit is essential for sialylation by cellular enzymes to occur. Copyright Taylor & Francis, Inc.

Novel mixed-heteroatom macrocycles via templating: A new protocol

A series of novel thiadiaza and triaza crown ether attached galactose- and glucose-based glycolipids is synthesized, applying a new strategy. The key step is the formation of α-chloroacetamido precursors (14 and 21) from selectively protected bis(cyanomethyl)-glycolipids (13 and 19) in two steps. The cyclization reaction furnishes good yields in relatively short times in aqueous ethanol or acetonitrile. To generalize this method, macrocycles 3 and 25 are reported as well. Attempts to use the traditional synthetic approaches for cyclization failed to provide reasonable yields.