Stereo- and regioselective radical cyclization of 6-(bromomethyl)dimethylsilyl-1',2'-unsaturated uracil nucleosides: Synthesis of 1'- -hydroxymethyl nucleosides | Zendy

Junko Ogamino | Zendy; Hiroki Kumamoto | Zendy; Hiroshi Mizunuma | Zendy; Shingo Takeda | Zendy; H. TANAKA | Zendy

Open Access

Stereo- and regioselective radical cyclization of 6-(bromomethyl)dimethylsilyl-1',2'-unsaturated uracil nucleosides: Synthesis of 1'- -hydroxymethyl nucleosides

Author(s) -

Junko Ogamino,

Hiroki Kumamoto,

Hiroshi Mizunuma,

Shingo Takeda,

H. TANAKA

Publication year - 2001

Publication title -

nucleic acids symposium series

Language(s) - English

Resource type - Journals

eISSN - 1746-8272

pISSN - 0261-3166

DOI - 10.1093/nass/1.1.3

Subject(s) - hydroxymethyl , stereoselectivity , uracil , regioselectivity , chemistry , uridine , anomer , derivative (finance) , stereochemistry , radical cyclization , organic chemistry , catalysis , dna , biochemistry , rna , financial economics , economics , gene

Mode of radicalcyclization (5-exovs. 6-endo) was investigated by using 6-(bromomethyl)dimethylsilyl derivatives of 1',2'-unsaturated uridine with an aim to develop a new stereoselective method for the introduction of an alpha-hydroxymethyl group at the anomeric position. Although the 2'-unsubstituted derivative underwent only 6-endo-cyclization, substrates bearing 2'-CO2Me or 2'-OBz group gave exclusively 5-exo-cyclized products with a high stereoselectivity.

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