Stereocontrolled hydroxymethylation of carbohydrate imines: Formal synthesis of destomic acid and lincosamine

Addition of [(dimethylphenylsilyl)methyl]magnesium chloride to 6-benzylimino-6-deoxy-1,2;3,4-di- O-isopropylidene-α- D-galactopyranose mediated by Ce(III)Cl 3 or CuI/BF 3·Et 2O proceeds with complete syn- or anti-diastereoselectivity, respectively, to afford highly chiral precursors of destomic acid...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 5; no. 11; pp. 2261 - 2264
Main Authors van Delft, Floris L., de Kort, Martin, van der Marel, Gijs A., van Boom, Jacques H.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.11.1994
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
STEREOSELECTIVE SYNTHESIS
REAGENTS
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Summary:Addition of [(dimethylphenylsilyl)methyl]magnesium chloride to 6-benzylimino-6-deoxy-1,2;3,4-di- O-isopropylidene-α- D-galactopyranose mediated by Ce(III)Cl 3 or CuI/BF 3·Et 2O proceeds with complete syn- or anti-diastereoselectivity, respectively, to afford highly chiral precursors of destomic acid or lincosamine. Addition of [(dimethylphenylsilyl)methyl]magnesium chloride to 6-benzylimino-6-deoxy-1,2;3,4-di- O-isopropylidene-α- D-galactopyranose mediated by Ce(III)Cl 3, or CuI/BF 3·Et 2O proceeds with excellent diastereoselectivity to give the syn or anti-adduct 1 and 2, respectively.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(00)86303-X