The first synthesis of a thioglycoside analogue of the immunostimulant KRN7000.
The first total synthesis of a thioglycoside analogue of KRN7000, a potential immunostimulant, is described. Two key intermediates are alpha-galactosyl thiol 4 and phytosphingosine derivative 5, which were both prepared from D-galactose.
Dere
Ravindra T
RT
Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland.
Zhu
Xiangming
X
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000737:chemistry; D005690:Galactose / Q000737:chemistry; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013865:Thioglycosides / Q000737:chemistry*
D000276:Adjuvants, Immunologic; D005699:Galactosylceramides; D013438:Sulfhydryl Compounds; D013865:Thioglycosides; C103873:KRN 7000; D005690:Galactose