147126-58-7

Basic information

• Product Name: OCTYL 2-ACETAMIDO-2-DEOXY-B-D-GLUCOPYRANOSIDE
• Synonyms: OCTYL 2-ACETAMIDO-2-DEOXY-B-D-GLUCOPYRANOSIDE;OCTYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE;OCTYL-2-ACETAMIDO-2-DEOXY-SS-D-GLUCOPYRANOSIDE;Octyl 2-(AcetylaMino)-2-deoxy-;Octyl 2-(AcetylaMino)-2-deoxy-β-D-glucopyranoside
• CAS NO: 147126-58-7
• Molecular Formula: C₁₆H₃₁NO₆
• Molecular Weight: 333.42
• EINECS: 1533716-785-6
• Product Categories: Carbohydrates & Derivatives;Detergents
• Mol File: 147126-58-7.mol

Chemical Properties

• Melting Point: 183-185?C
• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: OCTYL 2-ACETAMIDO-2-DEOXY-B-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: OCTYL 2-ACETAMIDO-2-DEOXY-B-D-GLUCOPYRANOSIDE(147126-58-7)
• EPA Substance Registry System: OCTYL 2-ACETAMIDO-2-DEOXY-B-D-GLUCOPYRANOSIDE(147126-58-7)

Safety Data

• Hazardous Substances Data: 147126-58-7(Hazardous Substances Data)

Usage

Uses

Used in Biochemistry:
OCTYL 2-ACETAMIDO-2-DEOXY-B-D-GLUCOPYRANOSIDE is used as a nonionic detergent for the solubilization of membrane-bound proteins. Its ability to interact with proteins without disrupting their structure makes it a valuable tool in the study and manipulation of biological systems.
Used in Pharmaceutical Industry:
OCTYL 2-ACETAMIDO-2-DEOXY-B-D-GLUCOPYRANOSIDE is used as a pharmaceutical compound for its potential therapeutic applications. Its unique structure allows it to interact with various biological targets, making it a promising candidate for the development of new drugs.
Used in Chemical Research:
As a complex organic molecule, OCTYL 2-ACETAMIDO-2-DEOXY-B-D-GLUCOPYRANOSIDE is used in chemical research to study its properties, reactivity, and potential applications in the synthesis of other compounds.
Used in Material Science:
The unique properties of OCTYL 2-ACETAMIDO-2-DEOXY-B-D-GLUCOPYRANOSIDE make it a candidate for use in the development of new materials with specific properties, such as improved solubility or stability in various environments.

Upstream product

• 111-87-5 octanol 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 173725-22-9 n-octyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 117177-19-2 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline 
• 14131-63-6 D-glucosamine hydrochloride 
• 70749-28-9 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-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 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 1040191-33-0 N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide 

Downstream Products

• 196876-39-8 1-octyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 624737-91-3 (R)-4-{(S)-2-[(R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-octyloxy-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester 
• 500767-98-6 (R)-4-{(S)-2-[(R)-2-((4aR,6R,7R,8R,8aS)-7-Acetylamino-2,2-dimethyl-6-octyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester 
• 196876-43-4 N-((2R,3R,4R,5S,6R)-4-Benzyloxy-5-hydroxy-6-hydroxymethyl-2-octyloxy-tetrahydro-pyran-3-yl)-acetamide 
• 196876-44-5 N-((2R,3R,4R,5S,6R)-4-Benzyloxy-6-cyanomethoxymethyl-5-hydroxy-2-octyloxy-tetrahydro-pyran-3-yl)-acetamide 
• 196876-41-2 N-((2R,3R,4R,5S,6R)-6-Benzyloxymethyl-4-cyanomethoxy-5-hydroxy-2-octyloxy-tetrahydro-pyran-3-yl)-acetamide 
• 196876-57-0 N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-5-((2S,3R,4S,5S,6R)-4-benzyloxy-3-cyanomethoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yl]-acetamide 
• 196876-51-4 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-cyanomethoxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 
• 196876-52-5 Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-4-cyanomethoxy-tetrahydro-pyran-3-yl ester 
• 196876-53-6 Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-cyanomethoxymethyl-tetrahydro-pyran-3-yl ester 
• 196876-58-1 Benzoic acid (2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-3-yl ester 
• 196876-59-2 Benzoic acid (2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-benzyloxymethyl-5-cyanomethoxy-tetrahydro-pyran-3-yl ester 
• 196876-50-3 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4R,5R,6R)-5-acetylamino-2-benzyloxymethyl-4-cyanomethoxy-6-octyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 
• 211567-28-1 N-((2R,4aR,6R,7R,8S,8aS)-8-Hydroxy-6-octyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide 

Relevant articles and documents

Straightforward glycosylation of alcohols and amino acids mediated by ionic liquid

Green glycosylation of functionalized alcohols and α-amino acids, using an ionic liquid as a recyclable solvent, was performed in one step directly from the unprotected monosaccharide under scandium triflate or ferric chloride catalysis. Pure α- and β-glycosides could be obtained after specific enzymatic hydrolysis.

Ionic liquid promoted atom economic glycosylation under Lewis acid catalysis

Straightforward glycosylation of various alcohols with unprotected and non-activated monosaccharides were performed under scandium triflate catalysis. Rate and yield of glycosylation were highly improved when using 1-butyl-3-methylimidazolium trifluoromethanesulfonate as a green solvent. This ionic liquid was allowed to be recycled at least three times without loss of activity. The possibility of drastically reducing the amounts of catalyst (down to 1 mol%) and aglycone (down to 1 equiv) when performing the reaction in ionic liquid opens new perspectives in O-glycosylation, as a direct coupling between an aglycone and free sugars.

Protecting group free glycosidations using p-toluenesulfonohydrazide donors

(Figure Presented) N-Glycopyranosylsulfonohydrazides are introduced as glycosyl donors for protecting group free synthesis of O-glycosides, glycosyl azides, and oxazolines. Mono- and disaccharides containing a reducing terminal N-acelylglucosamine residue were condensed with p-toluenesulfonylhydrazide to give the desired β-D-pyranose donors. These donors can be activated with NBS and then glycosidated with the desired alcohol or transformed to the oxazoline or glycosyl azide.

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.

Facile approach to 2-acetamido-2-deoxy-β-D-glucopyranosides via a furanosyl oxazoline

(Chemical Equation Presented) A concise and convenient route that may be easily scaled is reported for the preparation of unprotected β-glucopyranosides of N-acetyl-D-glucosamine. Reaction of a wide variety of alcohols with a reactive, readily prepared furanosyl oxazoline under acidic conditions affords the corresponding β-D-glucopyranosides in good to high yields. Primary alcohols gave only β-D-glucopyranosides. A mechanism is proposed for this transformation.

N-Acetylmuramyl-L-Alanyl-D-Isoglutamine Glycosides: Effect of Glycoside Bond Configuration and Aglycone on Biological Activity

Hexyl, octyl, and cyclohexyl β-glycosides and heptyl and cyclohexyl α-glycosides of muramyl dipeptide (MDP) were synthesized. Tests in vitro and in vivo revealed lower immunostimulating activities of MDP α-glycosides in comparison with the corresponding β-glycosides and MDP itself. In the case of alkyl β-glycosides, differences in hydrocarbon chain lengths (C4-C8) and in aglycone (aliphatic chain and aliphatic or aromatic ring) exerted no substantial effect on the immunostimulating activity.

Pseudosugars, 40: Synthesis of ether- and imino-linked octyl N-acetyl- 5a'-carba-β-lactosaminides and -isolactosaminides: Acceptor substrates for α-(1→3/4)-fucosyltransferase, and enzymatic synthesis of 5a'- carbatrisaccharides

Synthesis of ether-linked octyl 5a'-carba-β-lactosaminide 3 and - isolactosaminide 5 was carried out in seven steps, starting from the coupling products of 1,2-anhydro-5a-carba-β-D-mannopyranose derivative 7, and the oxide anions generated from the octyl N-acetyl-β-D-glucosaminide derivatives 13 and 16, respectively, under basic conditions. The 5a-carba-α-D- mannopyranose residues of the coupling products 17 and 26 were transformed into the β-D-gluco configuration through epimerization of the respective 2'- oxo derivatives 19 and 28, and selective reduction, and then into the β-D- galacto configuration by direct nucleophilic substitution of their 4',6'- dimesylates 23 and 31 with an acetate ion. Biological assay has shown that 3 is an acceptor substrate for human-milk α-(1→3/4)-fucosyltransferase and, interestingly, 5 is not. In addition, the imino-linked congeners 4 and 6 have been synthesized by coupling of the 4-amino-4-deoxy- and 3-amino-3-deoxy derivatives 37 and 41 of octyl N-acetyl-β-D-glucosaminide, and the carba- sugar epoxide 8, respectively, and subsequent deprotection. Compound 4 is a substrate while 6 is neither a substrate nor an inhibitor for fucosyltransferase. Small-scale enzymatic synthesis was carried out by treatment of 3 and 4 with GDP-fucose and milk fucosyltransferase, which resulted in conversion into the corresponding trisaccharides 47 and 48, respectively.

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

A new synthesis of O-glycosides from totally O-unprotected glycosyl donors

O-Glycosidation of the totally O-unprotected aldoses (D-glucose, D-galactose and D-mannose) and D-fructose in THF or 1,4-dioxane using anhydrous FeCl3 as promoter afforded either aldofuranosides 1, 3, 4 in good overall yields or exclusively β-D-fructopyranosides 7. Conversely α-D-aldopyranosides 2, 5 and 6 were obtained respectively from D-glucose, D-mannose and N-acetyl-D-glucosamine when the reactions were performed in the presence of BF3.OEt2 under ultrasonication.