T. D. Inch
Sep 1, 1967
Citations
1
Influential Citations
55
Citations
Journal
Carbohydrate Research
Abstract
Abstract Methods for the stereoselective synthesis and configurational assignment of asymmetric, benzylic carbon atoms have been investigated. The reaction between phenylmagnesium bromide and 3- O -benzyl-1,2- O -isopropylidene-α- d - xylo -pentodialdo-1,4-furanose in ether is highly stereoselective, giving a mixture of 3- O -benzyl-1,2- O -isopropylidene-5- C -phenyl-α- d - gluco -pentofuranose and 3- O -benzyl-1,2- O -isopropylidene-5- C -phenyl-β- l - ido -pentofuranose in the ratio 1:14.4. The stereoselectivity of the reaction was appreciably different when ether was replaced by tetrahydrofuran as solvent. The novel, crystalline sugars, 5- C -phenyl- d - gluco -pentose and 4- C -benzyl- d - xylo -tetrose are described.