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)

Flash point:

>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 activity

[α]25/D 12°, c = 2 in ethanol

Water Solubility 

Soluble in chloroform and ethanol. Insoluble in water.

BRN 

90781

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+/s3

InChIKey

LLPWGHLVUPBSLP-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 Reference

2873-29-2(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29329995

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:1,5-Anhydro-2-deoxy-D-arabino-hex-1-enitol triacetate
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Tri-O-acetyl-D-glucal Usage And Synthesis

Chemical Properties

white to off-white crystalline powder

Uses

A D-glucal derivative.

Uses

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.

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%.

Tri-O-acetyl-D-glucal(2873-29-2)Related Product Information

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• /
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