Tadanier J, Martin J R, Kurath P, Goldstein A W, Johnson P
Carbohydr Res. 1980 Feb;79(1):91-102. doi: 10.1016/s0008-6215(00)85134-4.
Selective 4-N-acylation of fortimicin B (2) has been accomplished by 4-N-acylation of 1,2',6'-tri-N-benzyloxycarbonylfortimicin B (4) followed by hydrogenolysis of the N-protecting benzyloxycarbonyl groups. In this manner, fortimicin B was converted into fortimicin A (1), and a series of 4-N-acylfortimicins B (3) was prepared for antibacterial assay. The key intermediate, 1,2',6'-tri-N-benzyloxycarbonylfortimicin B, was prepared either directly from fortimicin B or by converting fortimicin A into 1,2',6',2''-tetra-N-benzyloxycarbonylfortimicin A (6a), followed by selective hydrolysis of the 4-N-(N-benzyloxycarbonyl)glycyl group of the latter.
通过对1,2',6'-三-N-苄氧羰基福提霉素B（4）进行4-N-酰化，然后对N-保护的苄氧羰基进行氢解，实现了福提霉素B（2）的选择性4-N-酰化。通过这种方式，福提霉素B被转化为福提霉素A（1），并制备了一系列4-N-酰基福提霉素B（3）用于抗菌测定。关键中间体1,2',6'-三-N-苄氧羰基福提霉素B可直接由福提霉素B制备，也可通过将福提霉素A转化为1,2',6',2''-四-N-苄氧羰基福提霉素A（6a），然后选择性水解后者的4-N-（N-苄氧羰基）甘氨酰基来制备。
