2873-29-2

Basic information

• Product Name: Tri-O-acetyl-D-glucal
• Synonyms: 1,2-DIDEOXY-3,4,6-TRI-O-ACETYL-D-ARABINO-1-HEXENOPYRANOSE;1,2-DIDEOXY-3,4,6-TRI-O-ACETYL-D-ARABINO-1-HEXENOPYRANOSIDE;1,5-ANHYDRO-2-DEOXY-D-ARABINO-HEX-1-ENITOL 3,4,6-TRI-O-ACETYL ETHER;3,4,6-TRI-O-ACETYL-1,5-ANHYDRO-D-ARABINO-HEX-1-ENITOL;3,4,6-TRI-O-ACETYL-1,5-ANHYDRO-2-DEOXY-D-ARABINO-HEX-1-ENITOL;3,4,6-TRI-O-ACETYL-D-GLUCAL;(-)-TRI-O-ACETYL-D-GLUCAL;TRI-O-ACETYL-D-GLUCAL
• CAS NO: 2873-29-2
• Molecular Formula: C12H16O7
• Molecular Weight: 272.25
• EINECS: 220-709-0
• Product Categories: Sugars, Carbohydrates & Glucosides;chiral;Biochemistry;Glucose;Glycals;O-Substituted Sugars;Sugars;Carbohydrates & Derivatives
• Mol File: 2873-29-2.mol
• Article Data: 126

Chemical Properties

• Melting Point: 53-55 °C(lit.)
• Boiling Point: 335.31°C (rough estimate)
• Flash Point: >230 °F
• Appearance: White to off-white/Crystalline Powder
• Density: 1.2602 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4455 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• Water Solubility: Soluble in chloroform and ethanol. Insoluble in water.
• BRN: 90781
• CAS DataBase Reference: Tri-O-acetyl-D-glucal(CAS DataBase Reference)
• NIST Chemistry Reference: Tri-O-acetyl-D-glucal(2873-29-2)
• EPA Substance Registry System: Tri-O-acetyl-D-glucal(2873-29-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 2873-29-2(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white crystalline powder

Uses

Different sources of media describe the Uses of 2873-29-2 differently. You can refer to the following data:
1. A D-glucal derivative.
2. 3,4,6-Tri-O-acetyl-D-glucal acts as a building block for the synthesis of oligosaccharides in both solution and solid-phase. Further, it is used in the preparation of D-arabino-1,5-anhydro-2-deoxy-hex-1-enitol.

InChI:InChI=1/C12H16O7/c1-7(13)17-6-11-12(19-9(3)15)10(4-5-16-11)18-8(2)14/h4-5,10-12H,6H2,1-3H3/t10-,11-,12+/m1/s1

Upstream product

• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 95068-98-7 3,4,6-tri-O-acetyl-2-C:1-N-carbonyl-2-deoxy-N-(p-tolylsulfonyl)-α-D-glucopyranosylamine 
• 75868-36-9 2,3,4,6-tetra-O-acetyl-1-bromo-D-glucopyranosyl bromide 
• 108-24-7 acetic anhydride 
• 13265-84-4 D-glucal 
• 75-36-5 acetyl chloride 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 65982-19-6 2,3,4,6-tetra-O-acetyl-D-monnopyranosyl chloride 
• 67-56-1 methanol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 78-94-4 methyl vinyl ketone 
• 107-13-1 acrylonitrile 
• 292638-85-8 acrylic acid methyl ester 
• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 

Downstream Products

• 13265-84-4 D-glucal 
• 534-97-4 D-lyxo-hexulose phenylosazone 
• 35822-13-0 C₁₅H₂₂HgO₁₀ 
• 35822-14-1 C₁₅H₂₂HgO₁₀ 
• 3427-20-1 methyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside 
• 3427-20-1 methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside 
• 34254-51-8 ((2S,5R,6S)-5-acetoxy-6-methoxy-5,6-dihydro-2H-pyran-2-yl)methyl acetate 
• 3427-20-1 methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside 
• 6087-40-7 (2R,3S,4R,6S)-3,4-diacetoxy-2-(acetoxymethyl)-6-methoxytetrahydro-2H-pyran 
• 6087-41-8 methyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-hexopyranoside 
• 16740-98-0 tri-O-methyl-D-glucal 
• 118967-75-2 1-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2-hydroxy-4-methoxybenzene 
• 118967-76-3 1-(4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl)-2-hydroxy-4-methoxybenzene 
• 14675-51-5 p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 

Relevant articles and documents

A new catalyst for the reductive elimination of acylated glycosyl bromides to form glycals

Ethylene-N,N′-bis(salicylideneiminato(IV)) {VO(salen)} was developed as a catalyst for the reductive elimination of acylated glycosyl bromides to form glycals. VO(salen) to be an effective catalyst for the preparation of glycals on a multi-gram scale. The catalyst was green in colour and changed to brown as the reaction progress.

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A convenient synthesis of glycals employing in-situ generated Cp2TiCl

Reductive elimination of acetylated glycosyl bromides to the corresponding glycal is easily achieved by mixing the bromide with Cp2TiCl2 and Mn in THF, and hence does not require the separate preparation of Cp2TiCl using glove-box techniques.

Long-lived glycosyl-chromium(III) complex intermediates in aqueous medium. Preparation of pyranoid glycals

Acetylated glycosyl-chromium(III)L (L=EDTA, NTA, IDA) complex intermediates (1) were detected in aqueous medium, with half-life-times of 30-300 minutes. The decay of these intermediates led to glycals (7-9) of high purity in preparatively usable 70-90% yields.

Titanium(III) reagents in carbohydrate chemistry: Glycal and C-glycoside synthesis

Titanocene(III) chloride and zirconcene(III) chloride are effective and mild reagents for radical generation in organic synthesis. In carbohydrate chemistry, these species are useful for the conversion of glycosyl halides to glycals, and for the stereospecific preparation of C-glycosides. In all cases, the 1-glycosyl radical is an active intermediate, generated by reaction of carbohydrate substrates with the organometallic. (C) 2000 Elsevier Science Ltd.

Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement

Stereoselective glycosylation is challenging in carbohydrate chemistry. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside and α-sulfoxide-glucoside, respectively.

Preparation method of 3, 4, 6-O-triacetyl-D-glucal

The invention relates to a preparation method of Tri-O-acetyl-D-glucal, which mainly solves the problems of volatile reagent, irritant smell, high cost and the like in the existing method. The technical scheme of the invention is as follows: the preparation method of 3, 4, 6-O-triacetyl-D-glucal comprises the following steps: peracetylated D-glucose is prepared by catalyzing D-glucose in glacial acetic acid with strong acid; the peracetylated D-glucose is brominated by a glacial acetic acid solution of hydrogen bromide to obtain brominated peracetylated D-glucose; and the brominated peracetylated D-glucose is reduced by zinc powder in an ammonium chloride solution to obtain a final product 3, 4, 6-O-triacetyl-D-glucal. The product provided by the invention has important application in thefields of glycopeptides and other polypeptide drugs.

Addressing the Structural Complexity of Fluorinated Glucose Analogues: Insight into Lipophilicities and Solvation Effects

In this work, we synthesized all mono-, di-, and trifluorinated glucopyranose analogues at positions C-2, C-3, C-4, and C-6. This systematic investigation allowed us to perform direct comparison of 19F resonances of fluorinated glucose analogues and also to determine their lipophilicities. Compounds with a fluorine atom at C-6 are usually the most hydrophilic, whereas those with vicinal polyfluorinated motifs are the most lipophilic. Finally, the solvation energies of fluorinated glucose analogues were assessed for the first time by using density functional theory. This method allowed the log P prediction of fluoroglucose analogues, which was comparable to the C log P values obtained from various web-based programs.