The invention relates to a new process for the preparation of the sphingosine derivatives described in European Patent Application No. 146,810, of the formula: ##STR1## It comprises protecting D-galactose in the 4,6-position and oxidizing it to the corresponding D-threose protected in the 2,4-position, condensing an aliphatic chain (R.sup.3) onto the latter by a Wittig reaction, converting the free hydroxyl group into a azido group and splitting off the protective group, protecting the resulting 2-azido-1,3-dihydroxy compound selectively in the 1-position and blocking it in the 3-position, liberating the 1-hydroxy group again, glycosidating the resulting compound or the abovementioned 2-azido-1,3-dihydroxy compound with the 0-trifluoro- or 0-trichloro-acetimade or the 1-halogen derivative of a 2,3,4,6-0-tetraacyl-D-glucose, splitting off the acyl groups of these and the protective group in the 3-position, converting the azido group into an amino group and acylating the amino compound with a fatty acid R.sup.1 --OH. The process gives the compounds of the therapeutically more active D series in a high yield in relatively few stages without resolving diastereomers.
该发明涉及一种用于制备欧洲专利申请号146,810中描述的
鞘氨醇衍
生物的新工艺,其
化学式为:##STR1## 该工艺包括保护
D-半乳糖的4,6-位并将其氧化为相应的D-三糖在2,4-位保护,通过Wittig反应将一脂肪链(R.sup.3)与后者缩合,将游离的羟基转化为偶氮基并去除保护基,选择性地保护所得的2-偶氮基-1,3-二羟基化合物的1-位并在3-位阻断它,再次释放1-羟基,将所得化合物或上述2-偶氮基-1,3-二羟基化合物与0-三
氟乙酰胺或0-三
氯乙酰胺或2,3,4,6-0-四酰基-
D-葡萄糖的1-卤衍
生物发生糖苷化反应,去除这些的酰基团和3-位的保护基,将偶氮基转化为
氨基并用
脂肪酸R.sup.1 --OH酰化
氨基化合物。该工艺在相对较少的阶段内高产率地提供了治疗活性更高的D系列化合物,而无需分离对映异构体。