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618-65-5

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Structure and reactivity of glycosides: IV. Koenigs-Knorr synthesis of aryl β-D-glucopyranosides using phase-transfer catalysts
A series of acetylated aryl β-D-glucopyranosides were prepared in 12-63% yields from tetra-O-acetyl-α-D-glycopyranosyl bromide and phenols containing acyl, formyl, and hydroxy substituents, and also from sterically hindered phenols in the two-phase system chloroform-aqueous alkali in the presence of triethylbenzylammonium chloride. Hydroxyethylated sucrose and dibenzo-18-crown-6 do not behave as phase-transfer catalysts in glycosylation of phenols. 2001 MAIK "Nauka/Interperiodica".
Pavlov,Sokolov,Zakharov
p. 1811 - 1814
(2007/10/03)

Process for nucleophilic fluoroalkylation of aldehydes
Aryl difluoromethyl sulfone adds to alkehydes under phase transfer conditions to give novel substituted alcohols of the general formula wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.
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(2008/06/13)

PHASE-TRANSFER-CATALYZED D-GLUCOSYLATION:SYNTHESIS OF BENZOYLATED ARYL β-D-GLUCOPYRANOSIDES AND β-D-GLUCOPYRANOSYL-SUBSTITUTED CINNAMATES
Phase-transfer-catalysed D-glucosylation of chelated phenolic aglucons and substituted cinnamic acids, using 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl bromide, resulted in the stereospecific formation of benzoylated aryl β-D-glucopyranosides and substituted-β-D-glucopyranosyl cinnamates, respectively, in good yields.The results conclusively disproved an earlier report that the phase-transfer method requires a nonparticipating group at C-2 or C-6 in the carbohydrate moiety. 1,2,3,4,6-Penta-O-benzoyl-β-D-glucopyranose was obtained as a minor side-product in all of these reactions.The possible mechanism of the phase-transfer method is discussed.
Loganathan, Duraikkannu,Trivedi, Girish K.
p. 117 - 126
(2007/10/02)

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Chemical Properties

Appearance/Colour :pale yellow solid
Melting Point: 178 °C(lit.)
Boiling Point: 552 °C at 760 mmHg
Flash Point:212.6 °C
Density: 1.51g/cm³
Solubility:Methanol, Water
Storage Temp.:Inert atmosphere,Room Temperature
Refractive Index: -62 ° (C=0.8, H2O)
PKA: 12.77±0.70(Predicted)
Merck: 14,4628
BRN: 89596

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