| Popis: |
Starting from d -glucose and d -(−)-quinic acid (5) (1 S ,5 R ,6 S )-5-azido-6-benzyloxycyclohex-2-en-1-ol (3), and the structurally related α,β-unsaturated alcohols 7 and 8, respectively, were prepared. They have been transformed, by treatment with 3-chloroperoxybenzoic acid, into (1 R ,2 S ,3 R ,5 S ,6 R )-3-azido-2-benzyloxy-5,6-epoxycyclohexane-1-ol (4) and the two diastereoisomeric 4,5-isopropylidenedioxycyclohexane-1-ols 9 and 10. Thermal Claisen rearrangement of the allylic alkcohols 3, 7 and 8 resulted in the functionalized branched-chain cyclohexenyl acetamides 12, 13 and 14, respectively. The prepared new cyclitols are useful starting materials for further derivatization to obtain novel enzyme-inhibitors, including phosphorylated cyclitols with “second-messenger” properties. |
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