Abstract
d-Galactose was converted into the glycosylating agents 4-azido-2,3-di- O-benzyl-4-deoxy-6- O-propionyl-α- d-glucopyranosyl chloride ( 11) and the methyl β- d-thiopyranoside 19. Condensation of 11 with 2,5-diazido-1,6-di- O-benzoyl-2,5-di-deoxy- l-iditol in the presence of mercury salts gave 24% of 2,5-diazido-3- O-(4-azido-2,3-di- O-benzyl-4-deoxy-6- O-propionyl-α- d-glucopyranosyl)-1, 6-di- O-benzoyl-2,5-dideoxy- l-iditol. Methyl trifluoromethanesulfonate-promoted glycosylation of 1,3-diazido-2- O-benzyl-1,3-dideoxy-5,6- O-isopropylidene- d-gulitol with 19 in the presence of 2,6-di- tert-butyl-4-methylpyridine gave 1,3-diazido-4- O-(4-azido-2,3-di- O-benzyl-4-deoxy-6- O-propionyl-α- d- glucopyranosyl)-2- O-benzyl-1,3-dideoxy-5,6- O-isopropylidene- d-gulitol ( 42), whereas, in the absence of base, migration of the O-isopropylidene group occurred, affording 1,3-diazido-6- O-(4-azido-2,3-di- O-benzyl-4-deoxy-6- O-propionyl-α- d- glucopyranosyl)-2- O-benzyl-1,3-dideoxy-4,5- O-isopropylidene- d-gulitol in addition to 42.
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 callSimilar Papers
Disclaimer: 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.
