Syntheses of sporaricin analogues, 2-deoxy-4-N-glycyl-6-O-(alpha-nebrosaminyl)fortamine and its 3-de-O-methyl compound.
نویسندگان
چکیده
2-Deoxy-4-N-glycyl-6-O-(alpha-nebrosaminyl)fortamine (21) and 3-de-O-methyl-2-deoxy-4-N-glycyl-6-O-(alpha-nebrosaminyl)fortamine (27) were prepared starting from lividamine. The syntheses include four key steps, that is, transformation of 2-deoxystreptamine moiety of lividamine to 4-N,3-O-didemethyl-2-deoxyfortamine, selective 4-N-methylation of the new aminocyclitol moiety, selective attachment of a glycyl residue to the methylamino group at C-4 and selective amination at C-6'.
منابع مشابه
Synthesis of the pentasaccharide related to the repeating unit of the antigen from Shigella dysenteriae type 4 in the form of its methyl ester 2-(trimethylsilyl)ethyl glycoside.
Starting from D-mannose, D-glucose and L-fucose, the pentasaccharide derivative methyl 2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl-(1-->3)-2-O-acetyl-4,6-O-benzylidene-alpha-D-mannopyranosyl-(1-->3)-2-O-acetyl-6-O-benzyl-4-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-alpha-D-mannopyranosyl-(1-->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-beta-D-glucopyranosid]uronate was synthesized. This compound...
متن کاملSynthetic explorations towards 3-deoxy-3-fluoro derivatives of D-perosamine.
Based on a literature precedent, preparation of methyl 4-azido-3,4,6-trideoxy-3-fluoro-alpha-D-mannopyranoside (18) was attempted via fluorination of methyl 4-azido-2-O-benzyl-4,6-dideoxy-alpha-D-altropyranoside with diethylaminosulfur trifluoride (DAST). Contrary to expectations, the reaction took place with retention of configuration at the site of the fluorination yielding methyl 4-azido-2-O...
متن کاملSyntheses of 23-C-alkylidene, and 23-N-containing derivatives of 5-O-mycaminosyltylonolide.
Several derivatives of 5-O-mycaminosyltylonolide substituted at C-23 have been prepared; these are 23-deoxy-23-C-methylene (3), 23-deoxy-23-C-(methoxycarbonylmethylene) (5), 23-deoxy-23-C-(ethoxycarbonylmethylene) (7), and 23-deoxy-23-C-(butoxycarbonylmethylene) (9), 23-deoxy-23-C-[(2E)-3-(ethoxycarbonyl)-2-propenylene] (11), and 23-deoxy-23-(dimethylaminoimino) (13), and 14-de(hydroxymethyl)-1...
متن کاملSpecificities of enzymes of glycosylphosphatidylinositol biosynthesis in Trypanosoma brucei and HeLa cells.
A series of synthetic analogues of d-GlcN alpha 1-6-d-myo-inositol-1-HPO(4)-sn-1,2-dipalmitoylglycerol, consisting of 22 variants of the d-GlcN or lipid components, were tested in trypanosomal and human (HeLa) cell-free systems. The assays measured the abilities of the analogues to act as substrates or inhibitors of the enzymes of glycosylphosphatidylinositol biosynthesis downstream of GlcNAc-p...
متن کاملSynthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs.
Methanolysis of 2,4,6-tri-O-benzoyl-2,3-dibromo-3-deoxy-D-altrono-1,5-lactone gave methyl 3-bromo-3-deoxy-2,4,6-tri-O-benzoyl-alpha-D-ribo-hex-2-ulofuranosonat e (3) and the anomeric mixture of the analogous 4,6-di-O-benzoyl derivative, having HO-2 free. Compound 3 was subjected to debromination with tributyltin hydride and tributyltin deuteride in the presence of 2,2'-azo-bisisobutyronitrile a...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- The Journal of antibiotics
دوره 32 11 شماره
صفحات -
تاریخ انتشار 1979