Process for the synthesis of sphingosine

A method for the production of a sphingoid base according to formula

• 35
• in which
• R is a hydrocarbon chain having 5-50 carbon atoms, which may be a straight chain or branched, saturated or contain one or more double bonds, and which may contain one or more functional groups, and
• R1 and R2 may be the same or different and may be H or a hydrocarbon chain having 1-10 carbon atoms, which may be a straight chain or branched, saturated or contain one or more double bonds, and which may contain one or more functional groups,
• the method comprising the steps of
• dissolving a starting compound according to formula III or a salt thereof in a substantially inert solvent,
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• in which R1, R2, are as defined above
• R3 and R4 may be the same or different and may be H, OH, or a hydrocarbon chain having 1-10 carbon atoms, which may be a straight chain or branched, saturated or contain one or more double bonds, and which may contain one or more functional groups, and R′ is a hydrocarbon chain having 3-48 carbon atoms, which may be a straight chain or branched, saturated or contain one or more double bonds, and which may contain one or more functional groups, the functional groups being selected from a hydroxyl group, an alkoxy group, a primary, secondary or tertiary amine, a thiol group, a thioether or a phosphorous containing functional group,
• (1) protecting the NH2 group with a NH2 protecting group,
• (2) activating C-4 HR3 for an elimination reaction with C-5 HR4 group,
• (3) causing an elimination reaction to take place to form a double bond between the C-4 and C-5 carbon atom, and
• (4) removing the NH2 protecting group.