88065-99-0Relevant academic research and scientific papers
Use of Carbohydrate Derivatives for Studies of Phosphorus Stereochemistry. Part 8. Preparation and Some Reactions of 1,3,2-Oxazaphospholidine-2-ones and -2-thiones derived from 2-Deoxy-3,4,6-tri-O-methyl-2-methylamino-D-glucopyranose
Hall, C. Richard,Inch, Thomas D.,Pottage, Colin,Williams, Nancy E.,Campbell, Malcolm M.,Kerr, Patrick F.
, p. 1967 - 1975 (2007/10/02)
The four cyclic phosphorus esters from the reaction of MePSCl2 with 2-deoxy-3,4,6-tri-O-methyl-2-methylamino-D-glucopyranose (1) have been separated with difficulty, and structures assigned.Ring-opening of the isomers and subsequent detachment of the chir
Some Rearrangements of 2-Deoxy-3,4,6-tri-O-methyl-2-methylamino-D-glucose and Related Compounds in Basic Solution; a Novel Base-promoted N->O Migration of a Phosphonate Ester
Hall, C. Richard,Inch, Thomas D.,Williams, Nancy E.
, p. 1977 - 1981 (2007/10/02)
Treatment of 2-deoxy-2-methylamino-3,4,6-tri-O-methyl-D-glucose (1) with sodium alkoxides affords 1-methyl-5-methoxymethylpyrrole-2-carbaldehyde (2) presumably by a series of elimination reactions and keto-enol equilibrations which precede ring closure and elimination of water.Substitution of nitrogen in (1) to give e.g. 2-N--2-deoxy-2-methylamino-3,4,6-tri-O-methyl-D-glucose (8) interferes with the elimination sequence at an early stage so that when (8) is treated with sodium ethoxide a novel N->O migration of the phosphonate ester group occurs in a rapid reaction sequence which results in the conversion of (8) into 3-deoxy-2N-methyl-4,6-di-O-methyl-α,β-D-erythro-hexofuran-2-ulosylamine 1,1-diethyl acetal in high yield.The N->O migrations in this type of reaction involve P-N bond cleavage with retention of configuration at phosphorus, an unusual if not unique occurrence for reactions under basic conditions.
