Abstract
A stereoselective approach to the advanced precursor of (+)-myriocin, 3-deoxy-1,2:5,6-di- O-isopropylidene-3-methoxycarbonylamino-α- d-glucofuranose 3- C-carboxylic acid, via the [3,3]-sigmatropic rearrangement of allylic thiocyanates prepared from d-glucose is presented. From the observed results, supported by DFT calculations, we can conclude that the [3,3]-sigmatropic rearrangement of the thiocyanato group in allylic hexofuranosides is strongly influenced by the steric interaction of the 1,2- O-isopropylidene group in the transition states.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
