Syntheses of Chiralγ-Lactones fromd-andl-Arabinoses

Synthesis of Japonilure, the Pheromone of Japanese Beetle

“…Reductive desulfurization and hydrogenation of the C-C double bond were done at the same time by treatment of 5 with Raney nickel under a hydrogen atmosphere to give 6 in a 73% yield. Conversion from 6 to 1 proceeded in a same manner reported by NISHIDA et al 6 ) Comparison of the reported of the specific rotation of 1 2 • 6 ) with that of ours suggested our synthetic pheromone to be 100% optically pure.…”

Syntheses and1H-NMR Studies of Methyl 4,6-Di-O-glucopyranosyl-β-d-glucopyranosides Chirally Deuterated at the(l→6)-Linkage Moiety

“…19 ) Perkins et af.2°) have already reported an assumption for D-glucopyranoses that H-6proR would be assignable to the proton with larger vicinal couplings of two C-6 protons, since the tg conformer would be particularly unfavorable. Our results, including previous studies 8 , 9,21) show that this rule is valid for mono-D-glucoses, (1--+6)- EXPERIMENTAL Melting points (mp) were uncorrected. IR spectra were recorded on a Jasc?…”

Complete assignment of hyaluronan oligosaccharides up to hexasaccharides

“…As in D D-GlcNAc, H6proS always has the higher chemical shift in HA oligosaccharides. 20 Determination of the location of each GlcA and GlcNAc spin system within each oligosaccharide was initially achieved by comparison of the assignments made for the di-and trisaccharides (1,2,4) with progressively longer chains until the hexasaccharide 7 was reached. These sequential assignments were confirmed using sequence-specific NOEs to each GlcNAc N-H proton from the H-1 proton of the adjacent b-(1!3)-linked GlcA (all N-H and H-1 protons have distinctive chemical shifts in oligosaccharides 1-7).…”