Stereocontrolled synthesis of 2,3-anhydro-β-D-lyxofuranosyl glycosides

Organic Letters

Volumn 3, Issue 4, 2001, Pages 607-610

  Gadikota, Rajendrakumar Reddy ^a   Callam, Christopher S ^a   Lowary, Todd L ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; THIOGLYCOSIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GLYCOSYLATION; STEREOISOMERISM; SYNTHESIS;

GLYCOSIDES; GLYCOSYLATION; MOLECULAR STRUCTURE; STEREOISOMERISM; THIOGLYCOSIDES;

EID: 0035932033     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol007008y     Document Type: Article

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39. Other transient intermediates could also be involved. For example, the succinimide liberated from NIS could form a glycosyl succinimide species. However, we also view this as unlikely as such intermediates have been isolated as stable byproducts from other NIS promoted glycosylation reactions by us (Houseknecht, J. B.; McCarren, P. R.; Lowary, T. L., unpublished results) and others (Krog-Jensen, C.; Oscarsson, S. J. Org. Chem. 1996, 61, 1234). Accordingly, we do not feel such species are productive intermediates in the synthesis of these glycosides.
40. Other transient intermediates could also be involved. For example, the succinimide liberated from NIS could form a glycosyl succinimide species. However, we also view this as unlikely as such intermediates have been isolated as stable byproducts from other NIS promoted glycosylation reactions by us (Houseknecht, J. B.; McCarren, P. R.; Lowary, T. L., unpublished results) and others (Krog-Jensen, C.; Oscarsson, S. J. Org. Chem. 1996, 61, 1234). Accordingly, we do not feel such species are productive intermediates in the synthesis of these glycosides.
41. The β-anomer of 3 also provides the β-glycoside products exclusively in yields identical to that of 3, which is also consistent with the pathway proposed in Figure 6.
42. f is usually significant, >0.2.