147025-06-7

Usage

Uses

Used in Cleaning Products:
DODECYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is used as a surfactant and detergent in cleaning products for its ability to lower the surface tension of water, enhancing the cleaning efficiency and effectiveness of these products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, DODECYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is used as a dispersing agent to improve the solubility and stability of hydrophobic drugs, facilitating their formulation and administration.
Used in Drug Delivery Systems:
DODECYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is also being investigated for its potential as a drug delivery system, due to its capacity to solubilize and stabilize hydrophobic drugs, which can enhance their bioavailability and therapeutic outcomes.

Upstream product

• 108-24-7 acetic anhydride 
• 159302-84-8 n-dodecyl 2-amino-2-deoxy-β-D-glucopyranoside 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 112-53-8 1-dodecyl alcohol 
• 173725-26-3 n-dodecyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranoside 
• 112929-24-5 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 211567-22-5 dodecyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside 

Downstream Products

• 154564-64-4 dodecyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 824396-41-0 1-dodecyl 2-acetamido-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside 
• 211567-29-2 1-dodecyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside 
• 211567-35-0 Bis-(2-chloro-ethyl)-((3aR,4R,5aR,8R,9aR,9bS)-4-dodecyloxy-2-oxo-8-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-2λ⁵-phospha-cyclopenta[a]naphthalen-2-yl)-amine 
• 211567-26-9 Methanesulfonic acid (2R,4aR,6R,7R,8R,8aR)-7-acetylamino-6-dodecyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 195006-97-4 dodecyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside 
• 824396-58-9 N-[8-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yloxy)-6-dodecyloxy-2-styryl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 
• 824396-63-6 1-dodecyl 2-acetamido-3-O-benzyloxycarbonyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside 
• 824396-53-4 1-dodecyl 2-acetamido-3-O-benzyl-2-deoxy-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside 
• 824396-65-8 1-dodecyl 2-acetamido-2-deoxy-3-O-methanesulfonyl-(R)-4,6-O-(E-2-methyl-3-phenyl-2-propenylidene)-β-D-glucopyranoside 
• 824396-64-7 1-dodecyl 2-acetamido-2-deoxy-3-O-methanesulfonyl-(R)-4,6-O-(E-3-phenyl-2-propenylidene)-β-D-glucopyranoside 

Relevant academic research and scientific papers

Effect of Aglycon Structure on Saccharide Elongation by Cells

Alkyl N-acetyl-β-D-glucosaminide (GlcNAc primers) with different aglycon moieties were synthesized and used to determine the effect of the aglycon structure on cellular saccharide elongation. Dodecyl N-acetyl-β-D-glucosaminide (GlcNAc-C12), tridecan-7-yl N-acetyl-β-D-glucosaminide (GlcNAc-2C6), and pentacosan-13-yl N-acetyl-β-D-glucosaminide (GlcNAc-2C12) primers were synthesized by glycosylation of dodecan-1-ol, tridecan-7-ol, and pentacosan-13-ol, respectively, with peracetylglucosamine. These primers were introduced to mouse B16 melanoma cells to prepare glycolipids. After 48 h incubation, results showed that GlcNAc-C12 was elongated to give NeuAc-Gal-GlcNAc-C12. GlcNAc-2C6 was also elongated to afford Gal-GlcNAc-2C6 and NeuAc-Gal-GlcNAc-2C6. On the other hand, GlcNAc-2C12 primer was not elongated. Significantly, the results demonstrated that the amount of glycosylated product increased 1.5-times by modifying the aglycon structure of GlcNAc from C12 to 2 C6 despite having almost the same number of C-units.

Glycosylation of dodecyl 2-acetamido-2-deoxy-β-d-glucopyranoside and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside as saccharide primers in cells

Syntheses of oligosaccharides expressed on cells are indispensable for the improvement of the functional analyses of the oligosaccharides and their applications. We are developing saccharide primers for synthesizing oligosaccharides using living cells. In this study, dodecyl 2-acetamido-2-deoxy-β-d-glucopyranoside (GlcNAc-C12) and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside (LacNAc-C12) were examined for their abilities to prime the syntheses of neolacto-series oligosaccharides in HL60 cells. When GlcNAc-C12 was incubated with HL60 cells in serum-free medium for 2 days, 14 kinds of glycosylated products were collected from the culture medium. They were separated by high-performance liquid chromatography. The sequences of the products were determined to be neolacto-series oligosaccharides including LewisX, sialyl LewisX, polylactosamine, and sialylpolylactosamine by mass spectrometry. GlcNAc-C12 was also glycosylated by B16 cells and gave sialyllactosamine. Furthermore, LacNAc-C12 gave similar glycosylated products to GlcNAc-C12.

Synthesis and protective anti-infective action of anomeric lipophilic glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine

Anomeric pairs of α-and β-dodecyl, α-and β-(1-pentylhexyl), and α-and β-cyclododecyl glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) were synthesized. The starting β-D-glucosaminides were obtained by the oxazoline method, and the corresponding α-isomers, by the mercuric iodide-catalyzed glycosylation of alcohols with α-glucosaminyl chloride peracetate in nitromethane at ～90°C. No reliable differences between the stimulation of mouse resistance to the infection with Staphylococcus aureus (doses of 2, 20, and 200 μg/mouse) and Escherichia coli (doses of 0.05, 1, and 20 μg/mouse) with the MDP α-and β-glycosides were found. Pleiades Publishing, Inc., 2006.

N-ACETYLGLUCOSAMINE DERIVATIVES AND USE THEREOF

The present invention relates to An N-acetylglucosamine derivative represented by the following formula (1), and a hyaluronic acid production promoting agent containing the same and a skin external preparation containing the same: wherein R1 is a hydrogen atom or an alkyl group having 2 to 18 carbon atoms; R2, R3, and R4 are hydrogen atoms or acyl groups having 2 to 18 carbon atoms and may be all the same or different from others; the steric structure at position 1 may be α or β; provided that R1, R2, R3, and R4 must not be all hydrogen atoms. It is intended to provide an easily available hyaluronic acid production promoting agent and a skin external preparation whereby the production of hyaluronic acid can be promoted in the skin and thus the skin can be maintained in a vital and moist state so that it is expected that the human skin can be prevented from age.

Alkylating agents from sugars. Cyclophosphamides derived from 2-amino- 2-deoxy-D-allose

Cyclophosphamides derived from alkyl 2-amino-4,6-O-benzylidene-2-deoxy- β-D-allopyranosides have been synthesized with good yield by treatment of the corresponding 2-amino-2-deoxy-D-allose derivatives with bis(2- chloroethyl)phosphoramide dichloride. The ring-forming reaction took place with very high diastereoselectivity. Subsequent hydrogenolysis gave excellent yields of cyclophosphamides derived from alkyl 2-amino-2-deoxy-β-D- allopyranosides, with hydrophilicity greater than that of the precursors. The starting material was easily available from 2-acetamido-2-deoxy-D-glucose.

Synthesis and surface-active properties of some alkyl 2-amino-2-deoxy-β-D-glucopyranosides

Several alkyl 2-acetamido-2-deoxy-β-D-glucopyranosides were synthesized using either the oxazoline or the N-allyloxycarbonyl procedure.The latter procedure gave better yields with fatty alcohols and cholesterol.The derivatives thus prepared were partly of fully deprotected and their surface-active properties assessed.Keywords: 2-Amino-2-deoxy-D-glucose; Amphiphiles; Surfactant; 14C-labelled