Ascomycin, Immunomycin, L-683590, FK-520, FR-900520

长川霉素Chemical Name: [1R,9S,12S(1'R,3'R,4'R),13R,14S,17R,21S,23S,24R,25S,27R]-17-Ethyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1(E)-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0(4,9)]octacos-18(E)-ene-2,3,10,16-tetraone; [3S(1'R,3'R,4'R),4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS]-15,19-Epoxy-8-ethyl-5,19-dihydroxy-3-[2-(4-hydroxy-3-methoxycyclohexyl)-1(E)-methylvinyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-1,4,5,6,7,8,11,12,13,14,15,16,17,18,19,20,21,23,24,25,26,26a-docosahydro-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21-tetraone
CAS No. 104987-12-4
项目整合开发状态: Preclinical
项目研究机构: Fujisawa (Originator)
合成路线:The reaction of FK-506 (I) with Tbdms-Cl and imidazole gives the bis silylated compound (II),which is regioselectively monodesilylated by means of aq.HF in acetonitrile to yield the monosilylated compound (III).The silylation of (III) with 2-bromophenyldimethylsilyl chloride (IV) and imidazole affords the new disilylated compound (V),which is submitted to radical translocating/reducing conditions by means of Et3N/O2 or AIBN as radical initiator and Bu3Sn2H as deuterium source.Under these conditions a mixture of labeled compounds (VI) and (VII) is obtained.

合成路线:This mixture is desilylated by means of aq.HOAc in THF to yield from a 41:59 up to a 68:32 mixture of labeled and unlabeled FK-506.

合成路线:The reaction of ascomycin (I) with Tbdms-Cl and imidazole gives the bis silylated compound (II),which is regioselectively monodesilylated by means of aq.HF in acetonitrile to yield the monosilylated compound (III).The silylation of (III) with 2-bromophenyldimethylsilyl chloride (IV) and imidazole affords the new disilylated compound (V),which is submitted to radical translocating/reducing conditions by means of Et3N/O2 as radical initiator and Bu3Sn2H as deuterium source.Under these conditions a mixture of labeled compounds (VI) and (VII) is obtained where about 70% is the ascomycin labeled compound (VI) and 30% the aromatic labeled compound (VII).

合成路线:This mixture is desilylated by means of aq.HOAc in THF to yield a 53:47 mixture of labeled and unlabeled ascomycin.