7772-85-2

Basic information

• Product Name: ISO-PROPYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE
• Synonyms: ISO-PROPYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE;Isopropyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside;ISO-PROPYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-SS-D-GLUCOPYRANOSIDE;Isopropyl-2-acetamide-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside;1-Methylethyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside-3,4,6-triacetate;beta-D-Isopropyl 2-acetamido-2-deoxy-glucopyranoside 3,4,6-triacetate;Isopropyl 2-acetamido-2-deoxyglucopyranosidetriacetate
• CAS NO: 7772-85-2
• Molecular Formula: C₁₇H₂₇NO₉
• Molecular Weight: 389.39758
• EINECS: 1533716-785-6
• Mol File: 7772-85-2.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 520℃
• Flash Point: 268℃
• Appearance: /
• Density: 1.21
• CAS DataBase Reference: ISO-PROPYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ISO-PROPYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(7772-85-2)
• EPA Substance Registry System: ISO-PROPYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(7772-85-2)

Safety Data

• Hazardous Substances Data: 7772-85-2(Hazardous Substances Data)

Usage

General Description

ISO-PROPYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE is an organic chemical compound often used in scientific research. This synthetic derivative of glucopyranoside, constructed with an isopropyl group and multiple acetyl groups, is a 2-deoxy sugar and is part of the broader family of glycosides – molecules in which a sugar is bonded to another functional group via a glycosidic bond. While the compound's specific biochemical and physiological behaviors may vary based on the context of its use, it generally shares the characteristics of other glycosides, which can present a wide range of biological activities.

Upstream product

• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 14131-68-1 N-acetyl-D-glucosamine 
• 134308-33-1 2-methyl-(2-acetamido-3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyrano)-<2,1-d>-2-oxazoline 
• 67-63-0 isopropyl alcohol 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 112929-24-5 1,3,4,6-tetra-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-α-D-glucopyranose 
• 112929-24-5 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose 
• 104655-89-2 1-methylethyl 3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-β-D-glucopyranoside 
• 104655-87-0 3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-α-D-glucopyranosyl bromide 
• 14131-62-5 D-glucosamine hydrochloride 
• 146934-02-3 2-deoxy-2-(allyloxycarbonylamino)-α-D-glucopyranoside 
• 2873-29-2 D-glucal triacetate 
• 304865-93-8 3,4,6-tri-O-acetyl-2-deoxy-2-methoxycarbonyl-amino-α-D-glucopyranosyl trichloroacetimidate 
• 130259-39-1 1-methylethyl 3,4,6-tri-O-acetyl-2-deoxy-2-methoxycarbonylamino-β-D-glucopyranoside 

Downstream Products

• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 40592-88-9 isopropyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-glucopyranoside 

Relevant articles and documents

Glycosylation in flow: effect of the flow rate and type of the mixer

The influence of the flow rate and the mode of mixing of reagent solutions on the result of glycosylation of isopropyl alcohol with glycooxazoline in 1,2-dichloroethane in the presence of (±)-camphor-10-sulfonic acid was studied. No reaction products were observed at low flow rates (?0.043 mL h?1) when using two Comet X-01 micromixers. Under these conditions, the disaggregation of supramers of the reagents is apparently inefficient for the reaction between them to occur. However, when one of the Comet X-01 micromixers was replaced with a T-shaped adapter (at the same flow rate), the expected reaction products, glycoside and glycal, appeared in the reaction mixture. This apparently suggests a higher disaggregation of the supramers reagents under these conditions, which allows the chemical reaction between them to occur.

NOVEL TLR4 INHIBITORS FOR THE TREATMENT OF HUMAN INFECTIOUS AND INFLAMMATORY DISORDERS

The present invention relates to methods of treating infectious, inflammatory and post-traumatic disorders by administering various compounds newly discovered to have TLR4 inhibitory activity. In addition to methods of treatment, the present invention further provides for pharmaceutical compositions comprising said compounds, together with a suitable pharmaceutical carrier. Because TLR4 is the most upstream receptor in the pro-inflammatory LPS signaling cascade, treatments of the invention, which inhibit or antagonize TLR4 action, may avoid the pitfalls associated with other cytokine inhibitors that act further down the pathway and accordingly play a less specific (and perhaps non-critical) role.

Copper(II)-mediated activation of sugar oxazolines: Mild and efficient synthesis of β-glycosides of N-acetylglucosamine

2-Methyl-(3,4,6-tri- O-acetyl- 1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline (5) was reacted with glycosyl acceptors bearing primary (6, 8, 10, 20) or secondary hydroxy groups (12, 14, 16, 18) in the presence of anhydrous cupric bromide or cupric chloride at elevated temperature to provide 2-acet-amido-2-deoxy-β-D-glucopyranosides in 36-92% yield. The reaction conditions are milder than those previously described for oxazoline activation employing p-toluenesulfonic acid or ferric chloride. Treatment of the oxazoline with trimethylsilyl azide (22) and CuCl2 leads to 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide (23) in 69% yield. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).