Koós M, Steiner B, Langer V, Gyepesová D, Durík M
Institute of Chemistry, Slovak Academy of Sciences, Bratislava, Slovak Republic.
Carbohydr Res. 2000 Sep 8;328(2):115-26. doi: 10.1016/s0008-6215(00)00099-9.
(4R)-2,3-O-Isopropylidene-methylspiro[4,6-dideoxy-alpha-L-lyxo+ ++-hexopyranosid-4,5'-imidazolidin]-2',4'-dione and (4R)-2,3-O-isopropylidene-methylspiro[4,6-dideoxy-beta-D-ribo-h exopyranosid-4,5'-imidazolidin]-2',4'-dione were prepared under various reaction conditions starting from methyl 6-deoxy-2,3-O-isopropylidene-alpha-L-lyxo-hexopyranosid-4-++ +ulose. Corresponding alpha-amino acids methyl (4R)-4-amino-4-C-carboxy-4,6-dideoxy-alpha-L-lyxo-hexopyranosid e and methyl (4R)-4-amino-4-C-carboxy-4,6-dideoxy-beta-D-ribo-hexopyranoside were obtained from the above hydantoins by selective acid hydrolysis of the isopropylidene group, followed by basic hydrolysis of the hydantoin ring. The crystal structures of both hydantoin derivatives are also presented.
以6-脱氧-2,3-O-亚异丙基-α-L-来苏糖己吡喃糖苷-4-酮糖为起始原料，在不同反应条件下制备了(4R)-2,3-O-亚异丙基-甲基螺[4,6-二脱氧-α-L-来苏糖++++-己吡喃糖苷-4,5'-咪唑烷]-2',4'-二酮和(4R)-2,3-O-亚异丙基-甲基螺[4,6-二脱氧-β-D-核糖++++-己吡喃糖苷-4,5'-咪唑烷]-2',4'-二酮。通过亚异丙基的选择性酸水解，然后对咪唑烷环进行碱水解，从上述乙内酰脲获得了相应的α-氨基酸甲基(4R)-4-氨基-4-C-羧基-4,6-二脱氧-α-L-来苏糖++++-己吡喃糖苷和甲基(4R)-4-氨基-4-C-羧基-4,6-二脱氧-β-D-核糖己吡喃糖苷。还给出了两种乙内酰脲衍生物的晶体结构。
