Izquierdo, Isidoro; Plaza, Maria T.; Robles, Rafael; Mota, Antonio published the artcile< Synthesis of 4-octuloses. Part IV. Synthesis of 2-deoxy-4-octulose derivatives by highly diastereoselective alkylations of protected hexuloses>, COA of Formula: C6H10O5, the main research area is arabinohexosulopyranose xylohexosulofuranose Reformatskii reaction bromoacetate; deoxyoctulose preparation stereoselective alkylation.
Reformatskii reaction of 2,3:4,5-di-O-isopropylidene-β-D-arabino-hexos-2-ulopyranose with Me bromoacetate proceeded with high diastereoselectivity to give Me 2-deoxy-4,5:6,7-di-O-isopropylidene-β-D-manno-oct-4-ulo-4,8-pyranosonate and its -D-gluco isomer, in an ≈ 10:1 ratio. Configurations of the new stereogenic centers (C-3) were determined by reduction of their ester groups to the related 2-deoxy-4,5:6,7-di-O-isopropylidene-β-D-manno- and -D-gluco-oct-4-ulo-4,8-pyranose. When alkylation at C-1 was carried out with 2-lithio tert-Bu acetate, the corresponding tert-Bu esters were formed in an ≈ 5.4:1 ratio. The stereochem. of the esters was established by their reductions On the other hand, reaction of 2,3:4,5-di-O-isopropylidene-β-D-arabino-hexos-2-ulopyranose with Me methoxycarbonylmethylenedimethylsulfurane gave only Me 2,3-anhydro-4,5:6,7-di-O-isopropylidene-β-D-glycero-D-galacto-oct-4-ulo-4,8-pyranosonate. Reformatskii reaction of 2,3:4,6-di-O-isopropylidene-α-L-xylo-hexos-2-ulofuranose with Me bromoacetate proceeded with moderate diastereoselectivity to give Me 2-deoxy-4,5:6,8-di-O-isopropylidene-α-L-gulo-oct-4-ulo-4,7-furanosonate and its -L-ido isomer, in an ≈ 3.5:1 ratio. Configuration of the new stereogenic center (C-3) was determined by degradation to the known di-Me D-methoxymalate.
Tetrahedron: Asymmetry published new progress about Alkylation, stereoselective. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, COA of Formula: C6H10O5.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics