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Volumn , Issue 1, 2007, Pages 116-124

Study of the glycosidation properties of 1-thiomannosazidopyranosides and 1-thiomannosaziduronic acid esters

Author keywords

Mannosamine; Carbohydrates; Glycosylation; Mannuronic acids; Thioglycosides

Indexed keywords


EID: 33846058760     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600759     Document Type: Article
Times cited : (16)

References (73)
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    • This partial donor regeneration was only observed using donor 10 and acceptor 14
    • This partial donor regeneration was only observed using donor 10 and acceptor 14.
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    • We are aware of the fact that orthogonality in truth means that the two glycosides participating in a glycosylation event can be used as either donor or acceptor at will, depending on the conditions applied. Here we use the word orthogonal in accordance with common practice in synthetic carbohydrate chemistry, namely, to indicate that a donor glycoside (here hemiacetal 23) is condensed with an acceptor glycoside (thiouronic ester 9) which has an anomeric functional group that can be activated in its own right allowing a second glycosylation event (here condensation with acceptor 25) without the necessity of intermediate functional group manipulations. As such the orthogonal glycosylation strategy is complementary to the so-called chemoselective glycosylation in which both donor and acceptor have the same anomeric functionality. See for a comparison: J. D. C. Codée, R. E. J. N. Litjens, L. J. van den Bos, H. S. Overkleeft, G. A. van der Marel
    • We are aware of the fact that orthogonality in truth means that the two glycosides participating in a glycosylation event can be used as either donor or acceptor at will, depending on the conditions applied. Here we use the word orthogonal in accordance with common practice in synthetic carbohydrate chemistry, namely, to indicate that a donor glycoside (here hemiacetal 23) is condensed with an acceptor glycoside (thiouronic ester 9) which has an anomeric functional group that can be activated in its own right allowing a second glycosylation event (here condensation with acceptor 25) without the necessity of intermediate functional group manipulations. As such the orthogonal glycosylation strategy is complementary to the so-called "chemoselective glycosylation" in which both donor and acceptor have the same anomeric functionality. See for a comparison: J. D. C. Codée, R. E. J. N. Litjens, L. J. van den Bos, H. S. Overkleeft, G. A. van der Marel, Chem. Soc. Rev. 2005, 34, 769-782.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.