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Volumn 41, Issue 14, 2000, Pages 2391-2394

Synthesis of the C-glycosidic analog of adenophostin A, a potent IP3 receptor agonist, using a temporary silicon-tethered radical coupling reaction as the key step

Author keywords

[No Author keywords available]

Indexed keywords

ADENOPHOSTIN A; ADENOPHOSTIN A DERIVATIVE; CALCIUM CHANNEL STIMULATING AGENT; GLYCOSIDE; INOSITOL 1,4,5 TRISPHOSPHATE RECEPTOR; UNCLASSIFIED DRUG;

EID: 0034175619     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00171-4     Document Type: Article
Times cited : (31)

References (30)
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    • Synthetic studies of C-disaccharides using the temporary silicon-tethered radical coupling strategy: (a)
    • Synthetic studies of C-disaccharides using the temporary silicon-tethered radical coupling strategy: (a) Xin, Y. C.; Mallet, J.-M. M.; Sinay, P. J. Chem. Soc., Chem. Commun. 1993, 864-865. (b) Myers, A. G.; Gin, D. Y.; Rogers, D. H. J. Am. Chem. Soc. 1994, 116, 4697-4718. (c) Fairbanks, A. J.; Perrin, E.; Sinay, P. Synlett. 1996, 679-681. (d) Rekai, E.; Rubinstenn, G.; Mallet, J.-M. M.; Sinay, P. Synlett. 1998, 831-834. (e) Rubinstenn, G.; Mallet, J.-M. M.; Sinay, P. Tetrahedron Lett. 1998, 39, 3697-3700.
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    • Synthetic studies of C-disaccharides using the temporary silicon-tethered radical coupling strategy: (a) Xin, Y. C.; Mallet, J.-M. M.; Sinay, P. J. Chem. Soc., Chem. Commun. 1993, 864-865. (b) Myers, A. G.; Gin, D. Y.; Rogers, D. H. J. Am. Chem. Soc. 1994, 116, 4697-4718. (c) Fairbanks, A. J.; Perrin, E.; Sinay, P. Synlett. 1996, 679-681. (d) Rekai, E.; Rubinstenn, G.; Mallet, J.-M. M.; Sinay, P. Synlett. 1998, 831-834. (e) Rubinstenn, G.; Mallet, J.-M. M.; Sinay, P. Tetrahedron Lett. 1998, 39, 3697-3700.
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    • Synthetic studies of C-disaccharides using the temporary silicon-tethered radical coupling strategy: (a) Xin, Y. C.; Mallet, J.-M. M.; Sinay, P. J. Chem. Soc., Chem. Commun. 1993, 864-865. (b) Myers, A. G.; Gin, D. Y.; Rogers, D. H. J. Am. Chem. Soc. 1994, 116, 4697-4718. (c) Fairbanks, A. J.; Perrin, E.; Sinay, P. Synlett. 1996, 679-681. (d) Rekai, E.; Rubinstenn, G.; Mallet, J.-M. M.; Sinay, P. Synlett. 1998, 831-834. (e) Rubinstenn, G.; Mallet, J.-M. M.; Sinay, P. Tetrahedron Lett. 1998, 39, 3697-3700.
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    • Synthetic studies of C-disaccharides using the temporary silicon-tethered radical coupling strategy: (a) Xin, Y. C.; Mallet, J.-M. M.; Sinay, P. J. Chem. Soc., Chem. Commun. 1993, 864-865. (b) Myers, A. G.; Gin, D. Y.; Rogers, D. H. J. Am. Chem. Soc. 1994, 116, 4697-4718. (c) Fairbanks, A. J.; Perrin, E.; Sinay, P. Synlett. 1996, 679-681. (d) Rekai, E.; Rubinstenn, G.; Mallet, J.-M. M.; Sinay, P. Synlett. 1998, 831-834. (e) Rubinstenn, G.; Mallet, J.-M. M.; Sinay, P. Tetrahedron Lett. 1998, 39, 3697-3700.
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    • Synthetic studies of C-disaccharides using the temporary silicon-tethered radical coupling strategy: (a) Xin, Y. C.; Mallet, J.-M. M.; Sinay, P. J. Chem. Soc., Chem. Commun. 1993, 864-865. (b) Myers, A. G.; Gin, D. Y.; Rogers, D. H. J. Am. Chem. Soc. 1994, 116, 4697-4718. (c) Fairbanks, A. J.; Perrin, E.; Sinay, P. Synlett. 1996, 679-681. (d) Rekai, E.; Rubinstenn, G.; Mallet, J.-M. M.; Sinay, P. Synlett. 1998, 831-834. (e) Rubinstenn, G.; Mallet, J.-M. M.; Sinay, P. Tetrahedron Lett. 1998, 39, 3697-3700.
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    • 2,5 boat-like conformation and their addition reactions selectively give the corresponding α-substitution products due to the stereoelectronic effect: (a)
    • 2,5 boat-like conformation and their addition reactions selectively give the corresponding α-substitution products due to the stereoelectronic effect: (a) Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969-980. (b) Rychnovsky, S. D.; Powers, J. P.; Lepage, T. J. J. Am. Chem. Soc. 1992, 114, 8375-8384.
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    • 2,5 boat-like conformation and their addition reactions selectively give the corresponding α-substitution products due to the stereoelectronic effect: (a) Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969-980. (b) Rychnovsky, S. D.; Powers, J. P.; Lepage, T. J. J. Am. Chem. Soc. 1992, 114, 8375-8384.
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    • 3 as below, after converting them to the corresponding 5,2′-di-O-benzoates 7′ and 11′
    • 3 as below, after converting them to the corresponding 5,2′-di-O-benzoates 7′ and 11′.
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    • -).
    • -).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.