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- W2045494638 abstract "Ethynylation of periodate-oxidized 1,2-O-isopropylidene-α-D-glucofuranose gave 6,7-dideoxy-1,2-O-isopropylidene-β-D-ido-hept-6-ynofuranose (2) together with a proportion of the α-D-gluco analog 6; ozonolysis of 2 and 6 gave 1,2-O-isopropylidene-β-L-idofuranurono-6,3-lactone (8) and 1,2-O-isopropylidene-α-D-glucofuranurono-6,3-lactone (7), respectively. The heptyne 2 gave a crystalline 3,5-dibenzoate 3, which on ozonolysis gave 3,5-di-O-benzoyl-1,2-O-isopropylidene-β-L-idofuranuronic acid (4); saponification of 4 with methanolic sodium methoxide led to epimerization at C-5. Ethynylation of 3-O-benzyl-1,2-O-isopropylidene-5-aldehydo-D-xylo-pentodialdo-1,4-furanose (9) (characterized as its p-nitrophenylhydrazone, 13) gave a separable, 3:4 mixture of 3-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-α-D-gluco-hept-6-ynofuranose (14) and the β-L-ido epimer (10); ozonolysis of 14 and 10 followed by hydrogenolysis gave the lactones 8 and 7, respectively. Crystalline 5-benzoates 11 and 15 were obtained from 10 and 14, respectively. Ozonolysis of 11 gave 5-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranuronic acid (12); similar treatment of 15 gave the α-D-gluco analog (16) of 15. Hydrogenolytic cleavage of the benzyl groups, and catalytic de-esterification, of 12 and 16 led to mixtures of the lactones 7 and 8 through epimerization at C-5." @default.
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- W2045494638 date "1970-08-01" @default.
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- W2045494638 title "Ethynylation of 1,2-O-isopropylidene-α-D-xylo-pentodialdose derivatives. A synthetic route to uronic acids" @default.
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- W2045494638 doi "https://doi.org/10.1016/s0008-6215(00)80483-8" @default.
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