Glucosyl chloride preparation

Lemieux32 has pointed out that the preparation by Brig]36 of 3,4,6-tri-0-acetyl-2-0-trichloroacetyl- -D-glucosyl chloride (XXI) through the interaction of penta-O-acetyl-0-D-glucopyranose (XVIII) with phosphorus pentachloride can be rationalized on the basis of modern chemical... 

Thus, Hickinbottom17 was able to prepare methyl a-D-glucopyranoside (in approximately 70% yield) by reaction of 3,4,6-tri-0-acetyl-2-0-tri-chloroacetyl-/3-D-glucosyl chloride in methanol, with silver oxide as catalyst and acceptor for hydrogen chloride. 

The further application of the mercuric acetate method made possible the synthesis of primeverose [6-0-/3-D-xylosyl-D-glucose] and also isoprime-verose [6-O-a-D-xylosyl-D-glucose] from 2,3,4-tri-O-acetyl-a-D-glucosyl chloride and tri-O-acetyl-D-xylosyl bromide. After the preparation of these sugars in larger quantities, the naturally occurring primeverosides could... 

A number of A -(2,3,4,6-tetra-0-acetyl-j3-D-glycopyranosyl)-5-aralkylidene-rhodanines, which were prepared conventionally from the appropriate rhodanine and glucosyl chloride, have been shown to possess antibacterial activity. ... 

For the synthesis of the 6-phosphate of D-glucosamine, which is important for the biosynthesis of the mucopolysaccharides, several methods have recently been described . The iV-acetyl compound is also known . 2-Amino-2-deoxy-a-D-glucopyranosyl i-phosphate has been prepared with Ag3P04 as a Ca salt from acetocMorglucosamine (2-acetamido-3,4,6-triacetyl-2-deoxy-a-glucosyl chloride ). 

Direct C-glucosylation can also be effected by boiling methyl a-D-glucopyranoside in benzene in the presence of aluminum chloride and boron trichloride. In this way, 2,3,4,6-tetra-0-acetyl-/3-D-glucopyranosylbenzene was prepared in 32% yield.143 C-Glycosyla-... 

A number of very useful indirect methods are available for the preparation of /3-D-glycosides. Polyacetate esters of 2-amino-2-deoxy-D-glucosyl bromide can be used,146 but, for general use, the more stable chlorides are to be preferred, since there is then little tendency for acyl migration147 and they can yield a wider range of glycosides.148,149 Under certain circum-... 

RAPIDASE XC-T is an industrial grade enzyme preparation formulated to a standardized alpha amylase activity with water and sodium chloride. Alpha amylases catalyze the hydrolysis of alpha-1,4 glucosyl linkages in polysaccharides such as starch and glycogen. This enzyme product is used by the textile industry to improve the deslzing of cloth by hydrolyzing starch in the fiber coating. 

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