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First Example of 5/6-O-Linked Pseudosaccharides: Synthesis of Bicyclic Nucleosides Containing Azido or Extended Carbohydrate Moiety

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Title First Example of 5/6-O-Linked Pseudosaccharides: Synthesis
of Bicyclic Nucleosides Containing Azido or Extended
Carbohydrate Moiety
 
Creator Maity, Joy Krishna
Mukherjee, Subhranshu
Drew, Michael G B
Achari, Basudeb
Mandal, Sukhendu B
 
Subject Chemistry
 
Description Abstract—Treatment of the D-glucose-derived substrate 1 with sodium hydride in tetrahydrofuran provided 3,6-anhydro monosaccharide
2, along with the 5,6-ether linked pseudodisaccharide 3, and pseudotrisaccharide 4. However, reaction of 1 with sodium
ethoxide in ethanol afforded 2 as the sole product, elaborated to the bicyclic azidonucleosides 9 and 16. Acetylated bicyclic nucleosides
17–19 with extended carbohydrate residues have been synthesized from 3.
 
Date 2007
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/1103/1/CARBOHYDRATE_RESEARCH__342__(17)2511%2D2521;2007[7].pdf
Maity, Joy Krishna and Mukherjee, Subhranshu and Drew, Michael G B and Achari, Basudeb and Mandal, Sukhendu B (2007) First Example of 5/6-O-Linked Pseudosaccharides: Synthesis of Bicyclic Nucleosides Containing Azido or Extended Carbohydrate Moiety. Carbohydrate Research, 342 (17). pp. 2511-2521.
 
Relation http://dx.doi.org/10.1016/j.carres.2007.08.013
http://www.eprints.iicb.res.in/1103/