Photolabile protection of 1,2- and 1,3-diols with salicylaldehyde derivatives
(Chemical Equation Presented) 1,2- and 1,3-diols, including carbohydrates, can be readily caged as acetals of 5-methoxy- or 5-hydroxysalicylaldehydes. Irradiation of these acetals with 300 nm light results in their efficient (Φ = 0.2-0.3) cleavage, regenerating an aldehyde and a glycol in excellent chemical yield. Photoreactive 5-hydroxysalicylaldehyde acetals can be produced by mild in situ reduction of photostable p-quinone precursors.
Kostikov, Alexey P.,Popik, Vladimir V.
supporting information; experimental part
p. 5277 - 5280
(2009/06/18)
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