107222-91-3

Upstream product

• 107222-87-7 3-O-Benzyl-6-(benzyloxycarbonylamino)-6-desoxy-1,2-O-isopropyliden-L-glycero-β-L-ido-heptofuranuronsaeure-methylester 
• 107222-85-5 2-Benzyloxycarbonylamino-3-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-hydroxy-propionic acid 
• 107222-89-9 6-Acetamido-3-O-benzyl-6-desoxy-1,2-O-isopropyliden-L-glycero-β-L-ido-heptofuranuronsaeure-methylester 

Relevant academic research and scientific papers

Branched and Chain-Extended Sugars, XXXI. - Synthesis of the Deferri Form of the Oxygen Analogue of &δ1-Albomycin

The oxygen analogue of the deferri form of δ1-albomycin has been synthesized.Reaction of the xylo-dialdehyde 2 with the anion of the lithium salt 3 of N,N-bis(trimethylsilyl)glycine trimethylsilyl ester leads to the chain-extended sugar.In good stereochemical selectivity the desired 6-amino-6-desoxy-L-ido-hepturonic acid is isolated as derivative 8.After transformation of 8 into the 1-acetate 23 the nucleoside 26 is obtained by a modification of the Hilbert-Johnson reaction using the uracil derivative 24.N-Methylation of 26 gives 28 in good yield.The serine derivative 31 reacts with the deblocked amino compound 30 to yield the peptide nucleoside 32.The tripeptide 36, which contains three units of N5-acetyl-N5-hydroxyl-L-ornithine, is successfully linked to the partial deblocked compound 34 via the mixed carbonic anhydride method.Final hydrogenation of 37 gives the free deferri form of the oxygen analogue 38.