69515-91-9

Basic information

• Product Name: 1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose
• Synonyms: 2-Deoxy-1,3,4,6-tetra-O-acetyl-D-glucopyranose;2-Deoxy-D-arabino-hexopyranose 1,3,4,6-Tetraacetate;1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose
• CAS NO: 69515-91-9
• Molecular Formula: C₁₄H₂₀O₉
• Molecular Weight: 332.3
• Product Categories: Carbohydrates & Derivatives
• Mol File: 69515-91-9.mol
• Article Data: 20

Chemical Properties

• Melting Point: 70-74°C
• Appearance: /
• CAS DataBase Reference: 1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose(69515-91-9)
• EPA Substance Registry System: 1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose(69515-91-9)

Safety Data

• Hazardous Substances Data: 69515-91-9(Hazardous Substances Data)

Usage

Description

1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose is a white solid compound with the CAS number 69515-91-9. It is a derivative of D-glucopyranose, a monosaccharide, where four hydroxyl groups are acetylated at positions 1, 3, 4, and 6, and the hydroxyl group at position 2 is deoxylated (removed). This modification of the sugar structure provides unique chemical properties that make it useful in various applications.

Uses

Used in Organic Synthesis:
1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose is used as an intermediate in organic synthesis for the production of various complex organic molecules. Its unique structure allows for selective functionalization and modification, making it a valuable building block in the synthesis of bioactive compounds, pharmaceuticals, and other specialty chemicals.
Used in Pharmaceutical Industry:
1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose is used as a key component in the development of novel drugs, particularly in the design of glycoconjugates and other sugar-based therapeutics. Its unique structure can be exploited to enhance the activity, selectivity, and bioavailability of drug candidates, potentially leading to more effective treatments for various diseases.
Used in Chemical Research:
In the field of chemical research, 1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose serves as a model compound for studying the reactivity and properties of acetylated sugars. This knowledge can be applied to understand the fundamental chemistry of carbohydrates and their interactions with other molecules, which is crucial for the development of new materials and applications in various industries.
Used in Material Science:
The unique structure of 1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose can be utilized in the development of new materials with specific properties, such as improved stability, solubility, or biocompatibility. These materials can find applications in various fields, including coatings, adhesives, and composites, where the incorporation of sugar-derived structures can provide enhanced performance characteristics.

Upstream product

• 2873-29-2 D-glucal triacetate 
• 61-58-5 2-deoxy-D-arabino-hexopyranose 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 126873-07-2 methyl 3,4,6-tri-O-acetyl-2-deoxy-α/β-D-glucopyranoside 
• 1374966-46-7 (3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanato-tetrahydro-2H-pyran-2,4,5-triyl triacetate 
• 154-17-6 D-2-deoxyglucose 
• 83-87-4 D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 

Downstream Products

• 135700-54-8 S-phenyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-thiohexopyranoside 
• 90670-51-2 thiophenyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside 
• 3650-58-6 p-nitrophenyl 2-deoxy-α-D-arabino-hexopyranoside 
• 82205-95-6 1-(2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)-2-nitroimidazole 
• 1013036-33-3 C₄₁H₄₆O₁₂ 
• 1013036-25-3 C₂₀H₂₂O₇ 
• 1040917-27-8 p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-α-D-glucopyranoside 
• 209005-11-8 dibenzyl (3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl)phosphate 
• 141395-48-4 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α/β-D-glucopyranoside 
• 7226-42-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranoside 
• 2873-29-2 D-glucal triacetate 
• 117841-73-3 methyl (3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 1602920-98-8 p-tolyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→6)-2,3,4-O-benzyl-1-thio-β-D-glucopyranoside 
• 1602920-99-9 p-tolyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→6)-2,3,4-O-benzyl-1-thio-β-D-glucopyranoside 

Relevant articles and documents

Unexpected incorporation of bromine at a non-anomeric position during the synthesis of an O2-glycosylated diazeniumdiolate

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General Strategy for the Synthesis of Rare Sugars via Ru(II)-Catalyzed and Boron-Mediated Selective Epimerization of 1,2- trans-Diols to 1,2- cis-Diols

Human glycans are primarily composed of nine common sugar building blocks. On the other hand, several hundred monosaccharides have been discovered in bacteria and most of them are not readily available. The ability to access these rare sugars and the corresponding glycoconjugates can facilitate the studies of various fundamentally important biological processes in bacteria, including interactions between microbiota and the human host. Many rare sugars also exist in a variety of natural products and pharmaceutical reagents with significant biological activities. Although several methods have been developed for the synthesis of rare monosaccharides, most of them involve lengthy steps. Herein, we report an efficient and general strategy that can provide access to rare sugars from commercially available common monosaccharides via a one-step Ru(II)-catalyzed and boron-mediated selective epimerization of 1,2-trans-diols to 1,2-cis-diols. The formation of boronate esters drives the equilibrium toward 1,2-cis-diol products, which can be immediately used for further selective functionalization and glycosylation. The utility of this strategy was demonstrated by the efficient construction of glycoside skeletons in natural products or bioactive compounds.

Photolabile Protecting Group-Mediated Synthesis of 2-Deoxy-Glycosides

A green and efficient photolabile protecting group (PPG)-mediated glycosidation approach for the synthesis of 2-deoxy-glycosides is reported. By employing ortho-nitrobenzyl carbonate (oNBC) as PPG, N,N-dimethylformamide (DMF)-modulated SPhosAuNTf2/s

Substituted pyrazole compound, preparation method, pharmaceutical composition and applications thereof

The invention discloses a substituted pyrazole compound represented by a formula I, and a preparation method, a pharmaceutical composition and applications thereof, wherein the compound has characteristics of good stability, excellent solubility, low cytotoxicity and remarkable neuroprotective effect, can effectively prevent and treat nerve cell injury, and is an ideal medicinal compound for preventing or treating cerebral stroke, cerebral embolism, cerebral stroke sequelae, cerebral stroke dyskinesia, mitochondrial encephalomyopathy and amyotrophic lateral sclerosis of spinal cord.