Synthesis of threitol ceramide and [14C]threitol ceramide, non-glycosidic analogues of the potent CD1d antigen α-galactosyl ceramide

The synthesis of threitol ceramide, which is a non-glycosidic analogue of the potent CD1d antigen α-galactosyl ceramide, is described. The synthesis of a 14C-labelled threitol ceramide analogue is also presented. This radiolabelled analogue will allow the intracellular trafficking pattern/itinerary of this iNKT-CD1d cell agonist to be studied.

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(2S,3S,4R)-2-Azido-3,4-O-isopropylidene-1,3,4-octadecanetriolC21H41N3O3Ee = 100%[α]D22=+9.6 (c 1.0, CHCl3)Source of chirality: chiral poolAbsolute configuration: (2S,3S,4R)

1-O-[l-Threitol]-2-amino-1,3,4-d-ribo-octadecantriolC22H47NO6Ee = 100%[α]D22=+23 (c 1.0, CHCl3)Source of chirality: chiral poolAbsolute configuration: (2S,3S,4R,2′S,3′S)