2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide

2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide Basic information
Product Name:2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide
Synonyms:BROMO-2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSE;BROMO 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE;BROMO 2,3,4,6-TETRA-O-ACETYL-A-D-GLUCOPYRANOSE;2,3,4,6-O-tetraacetyl-α-D-glucopyranosyl bromide;Acetobromglucose;Acetobromo-α-D-glucose;Acetobromglucose;Tetraacetyl bromoglucose;Tetraacetyl bromoglucose;ACETOBROMO-ALPHA-D-GLUCOSE, STAB.
CAS:572-09-8
MF:C14H19BrO9
MW:411.2
EINECS:209-339-0
Product Categories:Sugars, Carbohydrates & Glucosides;13C & 2H Sugars;Biochemistry;Glucose;Halogenosugars;Sugars;Dextrins、Sugar & Carbohydrates;Carbohydrates & Derivatives;Carbohydrates;Glycon Biochem
Mol File:572-09-8.mol
2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide Structure
2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide Chemical Properties
Melting point 86-89 °C
alpha 194.5 º (c=2,chloroform)
Boiling point 0.125-30 °C(Press: 0.0005 Torr)
density 1.49±0.1 g/cm3(Predicted)
storage temp. −20°C
solubility Acetontrile (Very Slightly), Chloroform (Slightly), Methanol (Slightly)
form Powder
color White to beige
Water Solubility decomposes
Sensitive Moisture Sensitive
Merck 14,60
BRN 96669
Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKeyCYAYKKUWALRRPA-RGDJUOJXSA-N
CAS DataBase Reference572-09-8(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 24/25-36-26
WGK Germany -
8-10-21
HS Code 29329985
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide Usage And Synthesis
Chemical PropertiesWhite Fluffy Solid
UsesAn Intermediate in synthesis of ∫-glucosides
UsesAcetobromo-α-D-glucose acts as an intermediate in the preparation of beta-glucosides. It is also used as a possible poly(ethylene terephthalate) surface modification reagent to enhance its blood compatibility.
Purification MethodsIf nicely crystalline, recrystallise it from Et2O/pentane or pet ether (b 40-60o). Alternatively dissolve it in diisopropyl ether (dried over CaCl2 for 24hours, then over P2O5 for 24hours) by shaking and warming (for as short a period as possible), and filter warm. Cool to ca 45o, then slowly to room temperature and finally at 5o for more than 2hours. Collect the solid, wash it with cold dry diisopropyl ether and dry it in a vacuum over Ca(OH)2 and NaOH. Store it dry in a desiccator in the dark. Solutions can be stabilised with 2% CaCO3. [Redemann & Niemann Org Synth 65 236 1987, Coll Vol III 11 1955, Beilstein 17/6 V 368.]
2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide Preparation Products And Raw materials
Preparation Productsbeta-D-Glucopyranosylamine-->BENZYL ALPHA-D-GLUCOPYRANOSIDE-->1-AZIDO-1-DEOXY-BETA-D-GLUCOPYRANOSIDE-->1-AZIDO-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOSE-->ACETAGASTRODINE-->coniferin-->Emodin 6-O-β-D-glucoside-->N-NONYL-BETA-D-GLUCOPYRANOSIDE-->ETHYLVANILLINBETA-D-GLUCOPYRANOSIDE
Acetyl coenzyme A sodium salt Acetyl-resveratrol 2,5-DIDEOXY-2,5-IMINO-D-MANNITOL Acetylacetone Rocuronium bromide Acetoxyacetic acid SILICON TETRAACETATE Sodium triacetoxyborohydride Acetyl chloride alkyl polyglucoside Centchroman Sodium bromate Polydextrose Ethidium bromide Allyl bromide AMYLOGLUCOSIDASE 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide Methyl bromide

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