Big Chemical Encyclopedia

Chemical substances, components, reactions, process design ...

Articles Figures Tables About

Oxidation with pyridinium chlorochromate/aluminum

Further processing of 57 towards the ketone 60 is readily effected by highly regioselective tosylation of the primary hydroxyl group (66), hydride reduction 58 -> 59, and oxidation with pyridinium chlorochromate (PCC) on aluminum oxide to afford 60 in a yield of 70 % over the three steps (63). Due to the now practical accessibility of these furanoid building blocks supplementary modifications, that have already been performed, become preparatively relevant, e. g. the conversion of tosylate 58 into the 5,6-epoxide (66), C-extensions (63, 66), shortening of the carbon chain via periodation of 57 (63), and transformation of the respective products into acyclic derivatives by acid hydrolysis of the 1,2-0-isopropylidene group (63, 66). [Pg.68]

If the reaction takes place via an anion or in a S 2 fashion, high yields of the product alkyl-cyclopropanes have been obtained. Thus, reaction of methyl 4,6-( -benzyIidene-2,3-dideoxy-2,3-C-[(7 )-(chloromethyl)ethylidene]-a-D-mannopyranoside (1) with lithium aluminum hydride in refluxing tetrahydrofuran gave methyl 4,6-0-benzylidene-2,3-dideoxy-2,3-C-isopropylidene-a-D-mannopyranoside (2) in 89% yield. Similarly, treatment of chloromethylcyclopropane 3 with lithium triethylborohydride, followed by oxidation with pyridinium chlorochromate,. gave ishwarone (4) in 75% yield. ... [Pg.1727]


See other pages where Oxidation with pyridinium chlorochromate/aluminum is mentioned: [Pg.291]    [Pg.84]    [Pg.383]    [Pg.314]    [Pg.285]    [Pg.248]    [Pg.71]    [Pg.71]    [Pg.71]    [Pg.295]   


SEARCH



Aluminum oxidation

Aluminum oxide

Aluminum oxidized

Chlorochromate

Oxidation chlorochromate

Oxidation pyridinium chlorochromate

Oxidation with pyridinium chlorochromate

Pyridinium chlorochromate

Pyridinium chlorochromate oxidant

Pyridiniums oxidation

With pyridinium chlorochromate

© 2024 chempedia.info