100082-85-7Relevant articles and documents
Syntheses of Biologically Important Carbohydrates, 32. - Studies on the Preparation and Oxyamination of a Methyl-branched Pent-3-enopyranoside
Dyong, Ingolf,Tacken, Angelika
, p. 564 - 575 (2007/10/02)
The glycero-pent-3-enopyranoside 4c prepared in several steps from L-arabinose was transformed into the phenylsulfenic acid ester 4d which undergoes -sigmatropic rearrangement to give the 4-phenylsulfinyl derivative 5a.While the carbocyclic analogue 7c was easily methylated to give 8, subsequently rearranged, and subjected to phosphitolysis to yield the allyl alcohol derivative 6b, on similar treatment no reaction of 5a could be observed. - An alternative method started with the 2,3-epoxy-4-ulose 14 which was transformed into the ketone 11b, and this was methylated to give the epimers 9b and 10b.Both on treatment with thionyl chloride led to the glycal 13 as well as the desired 4-C-methyl-branched pent-3-enopyranoside 12.The glycero-pent-3-enopyranoside 4a could be transformed into the crystalline amino sugar components 18 and 19.