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• W2901359960 abstract "A convenient synthetic strategy to αGalCer and some relevant analogues by using a handily protected phytosphingosine is reported here. The conversion of the phytosphingosine amino group to azide and the protection of 3,4-diol as cyclic carbonate group, cleavable in mild basic conditions but resistant to acidic treatment, afforded quickly an excellent glycosyl acceptor. Its glycosylation with a proper galactosyl donor, gave a versatile intermediate in high yield and excellent stereoselectivity. To demonstrate the potentiality of the intermediate, three immunologically relevant compounds were chosen as model targets: αGalCer, dansyl alpha-galactosylceramide and 7DW8-5. These products were easily obtained in few steps and high yields to validate the synthetic route." @default.
• W2901359960 created "2018-11-29" @default.
• W2901359960 creator A5022261599 @default.
• W2901359960 creator A5050945191 @default.
• W2901359960 creator A5062220757 @default.
• W2901359960 date "2019-01-01" @default.
• W2901359960 modified "2023-10-01" @default.
• W2901359960 title "A versatile synthesis of αGalCer and its analogues exploiting a cyclic carbonate as phytosphingosine 3,4-diol protecting group" @default.
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• W2901359960 doi "https://doi.org/10.1016/j.carres.2018.11.005" @default.
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