Strategy synthesis with glycosyl phosphates

Dolichols (98), a family of polyisoprenoid alcohols, have isolated from all eukaryotic cells or archaebacteria." They play a role in the co-translational modification of proteins and are known in iV-glycosylation in the form of dolichol phosphate. The synthesis of the photochemical probes 118 and 119 bearing a photoreactive group [3-(trifiuoromethyl)-3-aryldiazirine], analogues of dolichol and dolichol phosphate, is described in Scheme 5.19. The synthetic strategy involves the sequential alkylation of a monoterpenoid hydroxysulfonyl dianion with allyl chlorides, and MBH adduct 102 as a starting material. 

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