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- W1990687948 abstract "The 5,6-isopropylidene acetal (3) of l-ascorbate 2-phosphate (4) was produced in almost quantitative yield by the action of phosphoryl chloride at 0–5° on 5,6-O-isopropylidene-l-ascorbate (2) in alkali (pH 12–13) containing a high concentration of pyridine. After hydrolytic cleavage of the 5,6-acetal group and removal of inorganic phosphate and chloride, compound 4 was isolated, without chromatographic purification, in 70% yield as its crystalline tricyclohexylammonium salt. When no pyridine was present during the reaction of 2 with phosphoryl chloride in an alkaline solution, it was converted into a mixture of 3 and bis(5,6-O-isopropylidene-l-ascorbate) 2,2'-phosphate-(5). Following removal of the 5,6-protecting groups of 5, the phosphoric diester 6 was isolated in pure form in 32% yield by fractional recrystallization of its barium salt from cold water. Reaction of 2 with phosphoryl chloride in acetone-pyridine gave, after removal of the protecting group, a mixture of four phosphoric esters that was resolved by column chromatography on an ion-exchange resin. Two of the products were identical to 4 and 5, and the third was tentatively identified as the 3-phosphate of l-ascorbic acid; the fourth was not identified. The structures of the phosphoric esters were established by elemental analysis, u.v. and n.m.r. spectroscopy (31P and 1H), and ionization constants." @default.
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- W1990687948 date "1978-11-01" @default.
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- W1990687948 title "Chemical synthesis of several phosphoric esters of l-ascorbic acid" @default.
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- W1990687948 doi "https://doi.org/10.1016/s0008-6215(00)83736-2" @default.
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