169333-09-9

Basic information

• Product Name: n-Dodecyl-β-D-galactopyranosid
• Synonyms: n-Dodecyl-β-D-galactopyranosid
• CAS NO: 169333-09-9
• Molecular Formula: C₁₈H₃₆O₅S
• Molecular Weight: 364.543
• Product Categories: Carbohydrates
• Mol File: 169333-09-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: n-Dodecyl-β-D-galactopyranosid(CAS DataBase Reference)
• NIST Chemistry Reference: n-Dodecyl-β-D-galactopyranosid(169333-09-9)
• EPA Substance Registry System: n-Dodecyl-β-D-galactopyranosid(169333-09-9)

Safety Data

• Hazardous Substances Data: 169333-09-9(Hazardous Substances Data)

Upstream product

• 25878-60-8 D-galactose pentaacetate 
• 112-55-0 1-dodecylthiol 
• 4163-60-4 β-D-galactose peracetate 
• 40591-65-9 2,3,4,6-tetra-O-acetylgalactopyranosyl-1-β-pseudothiourea hydrobromide 
• 19879-84-6 2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose 
• 495394-47-3 dodecyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 

Downstream Products

• 1061300-56-8 dodecyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 847370-79-0 dodecyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside 

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.

Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis

Here we report a method for the preparation of anomerically pure β-S-glycopyranosides (1,2-trans-glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl3 at reflux in the presence of a catalytic amount of InBr3. Deacylation of the intermediate peracetates were achieved under Zemplén conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose and disaccharides cellobiose, maltose, and lactose, were used as donors, and five thiols including an α/ω dithiol and Fmoc-L-cysteine were used as acceptors. Melting points, high res MS, [α]D and NMR data (1H and 13C, including COSY, HSQC and HMBC) are reported for compounds not previously described.

Synthesis of a tetrasaccharide repeating unit of O-antigenic polysaccharide of Salmonella enteritidis by use of unique and odorless dodecyl thioglycosyl donors

The first total synthesis of a unique tetrasaccharide repeating unit of lipopolysaccharide from Salmonella enteritidis has been accomplished by assembly of dodecyl thioglycosides. The crucial key steps were preparation of a rare branched dideoxy sugar, dtyvelose (3,6-dideoxy-d-arabino-d-hexose) and sequential regioselective glycosylation at 2,3-positions of a central d-mannose residue 5 with d-tyvelose 6 and d-galactose donors 7.

Synthesis of α-series ganglioside GM1α containing C20-sphingosine

A synthesis of α-series ganglioside GM1α (III 6Neu5AcGgOse4Cer) containing C20-sphingosine(d20:1) is described. Glycosylation of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-d- galactopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-d-glucopyranoside with the glucosamine donor ethyl 3-O-acetyl-2-deoxy-4,6-O-[(4-methoxyphenyl)methylene]- 2-phthalimido-1-thio-β-d-glucopyranoside furnished a β-(1→4)- linked trisaccharide. Reductive cleavage of the p-methoxybenzylidene group followed by intramolecular inversion of its triflate afforded the desired trisaccharide, which was transformed into a trisaccharide acceptor via removal of the phthaloyl and O-acetyl groups followed by N-acetylation. A tetrasaccharide acceptor was obtained by glycosylation of the trisaccharide acceptor with dodecyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-d-galactopyranoside, followed by removal of the p-methoxybenzyl group. Coupling of the tetrasaccharide acceptor with ethyl (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy- 1-thio-5-trichloroacetamido-d-glycero-d-galacto-2-nonulopyranosid)onate and subsequent radical reduction gave the desired GM1α saccharide derivative, which was coupled with (2S,3R,4E)-2-azido-3-O-benzoyl-4-eicosene-1,3-diol after conversion into the imidate.

Characterization of some mesogenic alkyl 1-thioglycosides

A series of dodecyl 1-thio-β-D-glycosides has been synthesized and characterized (DSC, NMR, CP MAS, X-ray diffraction) as possible new marking materials with liquid-crystalline properties. These compounds undergo solid to liquid crystal phase transitions at various temperatures, which depend on the nature of the carbohydrate part of the structure. Their liquid-crystalline phases show extreme shear thinning behaviour.

Amphiphilic Carbohydrate-Based Mesogens, 11 Synthesis of Mesogenic 1-Alkylthio-1-deoxy-D-galactitols by Glycoside Reduction

Alkyl-1-thio-α/β-D-galactopyranosides (hexyl-dodecyl, 1a-g) have been O-diethylborylated and then reduced with tetraethyldiboranes(6) in the presence of 9-methylsulfonyloxy-9-borabicyclononane (MSBBN) catalyst to give 1-alkylthio-1-deoxy-D-galactitols 3a-g after deprotection. 3 exhibit the smectic A liquid crystalline phase on melting. - Keywords: Carbohydrates, Liquid Crystals (Smectic), Alkyl-1-thio-α/β-D-galactopyranosides. 1-Alkylthio-1-deoxy-D-galactitols, Glycoside Reduction, X-Ray Diffraction (Small Angle)