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- W2023358725 abstract "Abstract The synthesis of (±)-6-deoxy-6-fluoro-chiro-inositol 2,3,5-trisphosphate (4) is reported, starting from cyclohexa-1,4-diene. A key step involved the stereospecific 1,4-addition of singlet oxygen to trans-1,2-di-O-(2-methoxyethoxymethyl)cyclohexa-3,5-diene-1,2-diol (7) to afford (±)-1,2,4/3-2,3-di-O-(2-methoxyethoxymethyl)cyclohex-5-ene-1,2,3,4-tetrol (9). Benzylation of 9 followed by osmylation and selective protection of the equatorial hydroxyl group gave (±)-1,4-di-O-benzyl-2,3,5-tri-O-(2-methoxyethoxymethyl)-chiro-inositol (12), which reacted with diethylaminosulphur trifluoride (DAST) with retention of configuration, to yield the 6-deoxy-6-fluoro derivative 13. Partial deprotection of 13, followed by phosphorylation and hydrogenolysis, gave 4." @default.
- W2023358725 created "2016-06-24" @default.
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- W2023358725 date "1992-10-01" @default.
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- W2023358725 title "Synthesis of racemic 6-deoxy-6-fluoro-chiro-inositol 2,3,5-trisphosphate" @default.
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- W2023358725 doi "https://doi.org/10.1016/0008-6215(92)85049-6" @default.
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