A process for the preparation of
sphingosine 1-
phosphate (11a) or a stereoisomer thereof, comprising the steps: (a) Conversion of L-
serine (1a) to methyl ester (2a) or a salt thereof: (b) protecting the amino function of methyl ester (2a) or the salt thereof to form methyl ester (3a),: where Pg stands for a
protecting group, (c) protecting the primary hydroxyl group and the amino group of methyl ester (3a) to form methyl ester (4a), where R 1 and R 2 independently of one another can be
hydrogen, an optionally substituted C1-C6
alkyl radical or an optionally substituted phenyl radical, or wherein R 1 and R 2 together can form an optionally substituted C4-C7 cycloalkyl radical (d) Reduction of methyl ester (4a) to form
alcohol (5a): (e) Oxidation of
alcohol (5a) to form
aldehyde (6a): (f) Reaction of
aldehyde (6a) with 1-pentadecyne and a base to form
alkyne (7a): (g) partial deprotection of
alkyne (7a) to form
alkyne (8a): (h) Reducing the
triple bond of alkyne (8a) to a trans
double bond to form
alkene (9a): (i) Phosphorylating the primary hydroxyl group of
alkene (9a) to form
phosphate (10a): and (j) Deprotection of
phosphate (10a) to form
sphingosine 1-phosphate (11a): wherein the method has at least one of the following features: Oxidation of
alcohol (5a) to form
aldehyde (6a) using
oxalyl chloride, DMSO and less than 5.5 equivalents of Hünig base, Oxidation of alcohol (5a) to form aldehyde (6a) at a temperature above -70°C, Reacting aldehyde (6a) with 1-pentadecyne and a base to form alkyne (7a) using at least 1.5 equivalents of 1-pentadecyne and / or Purification of the alkyne (7a), which is obtained after reacting aldehyde (6a) with 1-pentadecyne and a base to form alkyne (7a), by distilling off unreacted 1-pentadecyne.