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Tri-O-acetyl-D-glucal

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Company Name: Gill polypeptide biopharmaceutical (dalian) co., LTD  Gold
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Tri-O-acetyl-D-glucal manufacturers

  • peracetyl-D-gluca
  • peracetyl-D-gluca pictures
  • $1.00
  • 2026-09-12
  • CAS:2873-29-2
  • Min. Order: 1KG
  • Purity: 99.9%
  • Supply Ability: 500KG
Tri-O-acetyl-D-glucal 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;(-)-TRI-O-ACETYL-D-GLUCAL;TRI-O-ACETYL-D-GLUCAL;TRIACETYLGLUCAL
CAS:2873-29-2
MF:C12H16O7
MW:272.25
EINECS:220-709-0
Product Categories:Sugars, Carbohydrates & Glucosides;Biochemistry;Glucose;Glycals;O-Substituted Sugars;Sugars;chiral;Carbohydrates & Derivatives
Mol File:2873-29-2.mol
Tri-O-acetyl-D-glucal Structure
Tri-O-acetyl-D-glucal Chemical Properties
Melting point 53-55 °C(lit.)
Boiling point 335.31°C (rough estimate)
density 1.2602 (rough estimate)
refractive index 1.4455 (estimate)
Fp >230 °F
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
form Crystalline Powder
color White to off-white
Optical Rotation[α]25/D 12°, c = 2 in ethanol
Water Solubility Soluble in chloroform and ethanol. Insoluble in water.
BRN 90781
InChIInChI=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+/s3
InChIKeyLLPWGHLVUPBSLP-FHMMHVPQNA-N
SMILES[C@@H]1(OC(=O)C)[C@@H](COC(=O)C)OC=C[C@H]1OC(=O)C |&1:0,5,14,r|
CAS DataBase Reference2873-29-2(CAS DataBase Reference)
Safety Information
Safety Statements 24/25
WGK Germany 3
HS Code 29329995
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
1,5-Anhydro-2-deoxy-D-arabino-hex-1-enitol triacetate English
SigmaAldrich English
ACROS English
ALFA English
Tri-O-acetyl-D-glucal Usage And Synthesis
Chemical Propertieswhite to off-white crystalline powder
UsesA D-glucal derivative.
Uses3,4,6-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.
Synthesis

In a 500 mL round bottom flask add 10 g glucose, acetic acid 100 mL, acetic anhydride 32.5 mL, p-toluenesulfonic acid 0.5 g, ultrasonic reaction for 10 minutes, the above reaction solution add acetyl bromide 12.5 mL, methanol 9.0 mL, ultrasonic vibration, power 420W (model DST20500) reaction for 1 hour, TLC detection of the reaction is complete, add Dichloromethane was diluted, washed with water and recrystallized with ethanol to obtain 21.9 g of bromoglucose crystals with 96% yield.

In the above bromodextrose add -cyclodextrin 44 g, 220 mL of water and 11 g of zinc powder, ultrasonic power 480W, (model DST20500) oscillation reaction for 10 minutes, add ethyl acetate dilution, filtration, filtrate extracted with ethyl acetate for 3 times, combined with the organic phase, add anhydrous sodium sulfate drying, filtration, concentration under reduced pressure, the crude acetylated glucosinolates, and then recrystallized with ethyl acetate and petroleum ether to get acetylated glucose, and then recrystallized with ethanol and petroleum ether to get acetylated glucosinolates. And then recrystallized with ethyl acetate and petroleum ether to get acetylated glucosinolates pure product 13.8 g, the yield is 95%.

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