Tetrahedron p. 16747 - 16766 (1997)
Update date:2022-08-03
Topics:
Dubreuil, Didier
Cleophax, Jeannine
Vieira De Almeida, Mauro
Verre-Sebrie, Catherine
Liaigre, Jerome
Vass, George
Gero, Stephane D.
The synthesis of chiral protected D-6-deoxy-myo-inositol derivatives from D-galactose is described. Ferrier rearrangement of hexenogalactopyranosides has been employed to produce the corresponding 6- deoxy-cyclohexanone polyols. The stereoselectivity of the carbocyclic transformation was discussed on the basis of the experimental data and a mechanism has been proposed. From deoxy-inososes, the access to a variety of 6-deoxy and 3,6-dideoxy-myo-inositol was performed to prepare suitable monool, diol and triol precursors for the synthesis of D-deoxy-myo-inositol phosphate analogues.
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Doi:10.3987/com-98-8102
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(2017)
