10300-18-2Relevant articles and documents
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Farkas et al.
, p. 136,137,138 (1976)
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Reaction of 1,2-trans-glycosyl acetates with phosphorus pentachloride: New efficient approach to 1,2-trans-glycosyl chlorides
Ibatullin, Farid M.,Selivanov, Stanislav I.
, p. 9577 - 9580 (2007/10/03)
Reaction of phosphorus pentachloride with 1,2-trans-glycosyl esters is described. The reaction mechanism presumably involves formation of a tetrachlorophosphonium ion as one of the key reactive intermediates, which can be induced either by Lewis acids or by using acetonitrile as the reaction solvent. Two novel, efficient methods for the synthesis of the thermodynamically unstable glycosyl chlorides were developed based on this reaction.
REACTION OF GLYCOSYL HALIDES WITH BENZYL GRIGNARD REAGENTS: UNEXPECTED o-TOLYL ALKYLATION OF TETRA-O-ACETYLGLUCOPYRANOSYL BROMIDE AND DIRECT SYNTHESIS OF (β-GLYCOSYL)PHENYLMETHANES
Panigot, Michael J.,Curley, Robert W.
, p. 293 - 302 (2007/10/02)
The synthesis of (β-glycosyl)phenylmethanes by Grignard alkylation of glycosyl halides is investigated.Reaction of tetra-O-acetylglucopyranosyl bromide with benzylmagnesium chloride gave a good yield of a 3:1 mixture of 2-(β-D-glucopyranosyl)toluene and (β-glucosyl)phenylmethane.The requirement for an equatorial 2-acetoxy group and 6-acetoxymethyl group for the formation of the unexpected o-tolyl rearrangement product is explored by using xylosyl, mannosyl, and 2-deoxyglucosyl halides as substrates for the alkylation.Synthesis of (β-glucosyl)phenylmethane by alkylation of 2,3,4,6-tetra-O-benzylglucosyl bromide with benzylmagnesium chloride is also presented.