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2005
Carbohydrates
U 0500
Efficient and Selective Removal of Methoxy Protecting Groups in Carbohydrates.
A methodology to selectively cleave methoxy protecting groups next to hydroxy
05- 189 —
functions is described. The reaction is carried out with galactose, glucose, and rhamnose substrates. In the first step, the methoxy protecting group is transformed into a
methylenedioxy acetal or an O-methyl acetate, using a tandem radical hydrogen abstraction—oxidation reaction. The acetal groups are removed in good to excellent
yields. To simplify this methodology, an efficient one-pot protecting group transformation—cleavage reaction is developed. The resulting diols can be easily purified, and the
yields are similar to those obtained in the multi-step process. — (BOTO*, A.;
HERNANDEZ, D.; HERNANDEZ*, R.; SUAREZ, E.; Org. Lett. 6 (2004) 21,
3785-3788; Inst. Prod. Nat. Agrobiol., CSIC, Univ. La Laguna, E-38206 La Laguna,
Tenerife, Spain; Eng.) — Steudel
2005
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