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Introduction of Vinyl and Hydroxymethyl Functionalities at C-4 of Glucose-Derived Substrates: Synthesis of Spirocyclic, Bicyclic, and Tricyclic Nucleosides

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Title Introduction of Vinyl and Hydroxymethyl
Functionalities at C-4 of Glucose-Derived
Substrates: Synthesis of Spirocyclic, Bicyclic, and
Tricyclic Nucleosides
 
Creator Maity, Joy Krishna
Ghosh, Ramprasad
Drew, Michael G B
Achari, Basudeb
Mandal, Sukhendu B
 
Subject Chemistry
 
Description Installing hydroxymethyl and hydroxyethyl substitutions at
C-4 through vinylation and hydroboration-oxidation reactions
of the C-4 bis-hydroxymethyl derivative of D-glucose
based substrate, and inserting heteroatoms thereafter permitted
formation of N-, O-, or S-heterocycles leading to [4,5]-
or [5,5]-spirocycles and a bicyclo[3.3.0]octane product. Some
of the spirocycles were converted to spironucleosides under
Vorbru¨ggen glycosidation reaction conditions. Similarly, the
bicyclic product was elaborated to the corresponding bicyclic
nucleoside as well as an unexpected tricyclic nucleoside.
 
Date 2008
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/228/1/JOURNAL_OF_ORGANIC_CHEMISTRY%2C73_(11)%2C4305%2D4308%2C2008[71].pdf
Maity, Joy Krishna and Ghosh, Ramprasad and Drew, Michael G B and Achari, Basudeb and Mandal, Sukhendu B (2008) Introduction of Vinyl and Hydroxymethyl Functionalities at C-4 of Glucose-Derived Substrates: Synthesis of Spirocyclic, Bicyclic, and Tricyclic Nucleosides. The Journal of Organic Chemistry, 73 (11). pp. 4305-4308.
 
Relation htp://dx.doi.org/10.1021/jo8002826
http://www.eprints.iicb.res.in/228/