104206-19-1Relevant articles and documents
Synthesis of a carbohydrate-derived hydroxamic acid inhibitor of the bacterial enzyme (LpxC) involved in lipid A biosynthesis
Li, Xuechen,Uchiyama, Taketo,Raetz, Christian R. H.,Hindsgaul, Ole
, p. 539 - 541 (2007/10/03)
(Matrix presented) The enzyme LpxC (UDP-3-O-[(R)-3-hydroxymyristoyl] -GlcNAc deacetylase) catalyzes the second step of lipid A biosynthesis and is essential for bacterial growth. A GlcNAc-derived hydroxamic acid inhibitor 8 of this enzyme was synthesized
1,6-Anhydro-β-D-glucopyranose in organic synthesis: preparation of a fragment for the synthesis of rosaramycin
Procter, Garry,Genin, Denis,Challenger, Stephen
, p. 81 - 92 (2007/10/02)
1,6-Anhydro-β-D-glucopyranose has been used as the starting material for a synthesis of ethyl (E)-4-C-allyl-2,3,4,6-tetradeoxy-5,7-O-isopropylidene-8-O-methanesulphonyl-2,6-di-C-methyl-D-gulooct-2-enonate, which represents a synthetic unit equivalent to C-2/9 of the macrolide antibiotic rosaramycin.The synthesis involved a minimum of chromatography, and the extremely high level of regiochemical and stereochemical control was achieved by the use of epoxides at crucial C-C-bond-forming steps.A method was also developed, using tosylmethyl isocyanide, which converted a carbohydrate 6-aldehyde (19) directly into the corresponding homologated methyl ether.
