173725-22-9

Usage

Uses

Used in Organic Synthesis:
OCTYL-2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows it to be a versatile building block in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, OCTYL-2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is used as a key intermediate in the synthesis of drug candidates. Its unique structure and functional groups make it a valuable component in the development of new drugs with novel therapeutic properties.
Used in Agrochemical Industry:
OCTYL-2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is also used in the agrochemical industry as a starting material for the synthesis of new pesticides and other agrochemical products. Its unique structure and reactivity make it a promising candidate for the development of innovative and effective agrochemicals.
Used in Specialty Chemicals:
In the specialty chemicals industry, OCTYL-2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is used as a building block for the synthesis of various specialty chemicals, such as surfactants, polymers, and other high-value compounds. Its unique properties make it a valuable component in the development of new and innovative specialty chemicals.

Upstream product

• 111-87-5 octanol 
• 3006-60-8 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 
• 70749-28-9 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 27526-42-7 phenyl 2-acetamido-3,4,6-tri-O-acetyl-1,2-di-deoxy-1-thio-β-D-glucopyranoside 
• 128902-88-5 pent-4-enyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 14131-63-6 D-glucosamine hydrochloride 

Downstream Products

• 147126-58-7 octyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside 
• 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 
• 196876-39-8 1-octyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 211567-34-9 Bis-(2-chloro-ethyl)-((3aR,4R,5aR,8R,9aR,9bS)-4-octyloxy-2-oxo-8-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-2λ⁵-phospha-cyclopenta[a]naphthalen-2-yl)-amine 
• 211567-25-8 Methanesulfonic acid (2R,4aR,6R,7R,8R,8aR)-7-acetylamino-6-octyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 211567-31-6 1-octyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside 
• 198202-28-7 octyl (2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl)-(1->3)-2-acetamido-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 198202-22-1 octyl <2,4,6-tri-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl>-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 

Relevant academic research and scientific papers

Direct chemical glycosylation with pentenyl- and thioglycoside donors of N-acetylglucosamine

The use of pentenyl and thiophenyl glycosides of N-acetylglucosamine (GlcNAc) as glycosyl donors for the direct preparation of O-glycosides of GlcNAc promoted by N-iodosuccinimide (NIS) and metal triflates in dichloromethane has been investigated. Both glycosyl acceptors 1-octanol and (-)-menthol resulted in good glycosylation yields for both types of donors with pentenyl glycosides being somewhat superior in terms of yield. Carbohydrate-based acceptors were reacted with a benzylated GlcNAc-pentenyl donor but only provided disaccharides in poor to moderate yields. The results show that a variety of metal triflates are capable of acting as an activator for both NIS and the intermediate oxazoline.

H2so4-silica promoted direct formation of β-glycosides of N-Acetyl glycosylamines under microwave conditions

N-Acetyl glycosamines are important building blocks for the synthesis of biologically active oligosaccharides. This communication describes a simple direct protocol for the synthesis of βglycosides of N-acetyl glycosylamines from easily accessible perO-ac

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.

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.

The synthesis of glycosides of 2-acetamido-2-deoxyglucose catalyzed by mercuric iodide

The glycosylation of various alcohols with peracetylated α-D-glucosaminyl chloride catalyzed with mercuric iodide was studied along with the dependence of the reaction course on temperature, solvent, and quantity of catalyst. At room temperature, only β-glycosides of peracetylated N-acetylglucosamine were shown to result in dichloroethane or nitromethane with high yields. At 90-95°C, anomerization was observed, which led to the corresponding α-glycosides. The possibility of the synthesis of disaccharides with the β1→6 bond catalyzed by mercuric iodide was demonstrated.

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.

Iodine: A versatile reagent in carbohydrate chemistry III. Efficient activation of glycosyl halides in combination with DDQ1

Iodine, either alone or in combination with DDQ, has been found to serve as a very efficient reagent for the conversion of 'disarmed' glycosyl halides into simple 1,2-trans-glycosides. This reagent system represents a practical alternative to traditional

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