173725-22-9

Basic information

• Product Name: OCTYL-2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE
• Synonyms: OCTYL-2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE;OCTYL-2-ACETAMIDO-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE;Octyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside;OCTYL-2-ACETAMIDO-TRI-O-ACETYL-2-DEOXY-SS-D-GLUCOPYRANOSIDE;Octyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside;Octyl 2-(AcetylaMino)-2-deoxy-β-D-glucopyranoside 3,4,6-Triacetate
• CAS NO: 173725-22-9
• Molecular Formula: C₂₂H₃₇NO₉
• Molecular Weight: 459.53048
• Product Categories: Carbohydrates & Derivatives
• Mol File: 173725-22-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 576.195 °C at 760 mmHg
• Flash Point: 302.272 °C
• Appearance: /
• Density: 1.15 g/cm³
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: OCTYL-2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: OCTYL-2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(173725-22-9)
• EPA Substance Registry System: OCTYL-2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(173725-22-9)

Safety Data

• Hazardous Substances Data: 173725-22-9(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Octyl 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside (cas# 173725-22-9) is a compound useful in organic synthesis.

Upstream product

• 27526-42-7 phenyl 2-acetamido-3,4,6-tri-O-acetyl-1,2-di-deoxy-1-thio-β-D-glucopyranoside 
• 111-87-5 octanol 
• 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 
• 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 

Downstream Products

• 211567-31-6 1-octyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside 
• 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 
• 211567-34-9 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 
• 196876-39-8 1-octyl 2-acetamido-4,6-O-benzylidene-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 
• 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 
• 222191-79-9 octyl 3,6-di-O-acetyl-2-acetamido-2,4-dideoxy-4-(2,3,4,6-tetra-O-acetyl-1-deoxy-5a-carba-β-D-glucopyranos-1-yl)amino-β-D-glucopyranoside 

Relevant articles and documents

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.

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.

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.