Chiral Carbocyclic Nucleosides from D-Glucose: Enantiodivergent Synthesis and One-Pot Entry of Dimethylamino Functionality in the Purine Rings
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
View Archive Info| Field | Value | |
| Title |
Chiral Carbocyclic Nucleosides from D-Glucose: Enantiodivergent
Synthesis and One-Pot Entry of Dimethylamino Functionality in
the Purine Rings
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| Creator |
Roy, Atanu
Chakrabarty, Kuheli Dutta, Pradeep K Bar, Narayan C Basu, Nupur Achari, Basudeb Mandal, Sukhendu B |
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| Subject |
Chemistry
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| Description |
Cyclization of appropriately designed enose-nitrones derived from D-glucose, having nitrone at
C-5 or C-1 and allylic/homoallylic functionalities at C-3 of the sugar backbone, afforded polyhydroxylated
aminocarbocycles which were subsequently used as the precursors for carbocyclic
nucleoside analogues (11, 13, 16, 21, and 23). The enantiodirecting synthesis of both the
enantiomeric pairs of nucleoside analogues 11 and 13, 21a and 23a, and 21c and 23c, has also
been demonstrated by judiciously applying intramolecular nitrone cycloaddition (INC) reaction.
An interesting observation was that in the cyclization reaction of pyrimidine ring to purine ring in
DMF solvent, the substitution of C-6 chloro group with a dimethylamino functionality also occurred
spontaneously under mild condition, though similar reactions are reported to occur at higher
temperature. The hydrogen bonding between N-3 of the purine ring and an appropriate hydroxy
substituent in the carbocycle seems to play a crucial role in this reaction.
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| Publisher |
American Chemical Society
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| Date |
1999
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://www.eprints.iicb.res.in/692/1/JOURNAL_OF_ORGANIC_CHEMISTRY_64_(7)2304%2D2309;1999[61].pdf
Roy, Atanu and Chakrabarty, Kuheli and Dutta, Pradeep K and Bar, Narayan C and Basu, Nupur and Achari, Basudeb and Mandal, Sukhendu B (1999) Chiral Carbocyclic Nucleosides from D-Glucose: Enantiodivergent Synthesis and One-Pot Entry of Dimethylamino Functionality in the Purine Rings. The Journal of Organic Chemistry, 64 (7). pp. 2304-2309. |
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| Relation |
http://dx.doi.org/10.1021/jo981955r
http://www.eprints.iicb.res.in/692/ |
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