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Volumn 16, Issue 1, 2005, Pages 105-119

Disarming, non-participating 2-O-protecting groups in manno- and rhamnopyranosylation: Scope and limitations of sulfonates, vinylogous esters, phosphates, cyanates, and nitrates

Author keywords

[No Author keywords available]

Indexed keywords

CYANIC ACID DERIVATIVE; ESTER DERIVATIVE; NITRIC ACID DERIVATIVE; PHOSPHORUS DERIVATIVE; THIOGLYCOSIDE; TRIFLUOROMETHANESULFONIC ACID;

EID: 12344274639     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.11.032     Document Type: Article
Times cited : (68)

References (111)
  • 16
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    • B. Ernst G.W. Hart P. Sinaÿ Wiley-VCH Weinheim
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    • Pozsgay, V.1
  • 35
    • 0033555205 scopus 로고    scopus 로고
    • Note that although sulfonates are widely thought of as non-participating, recent examples of possible participation in simple displacement reactions of 1,2-dimesylates suggest that this is not necessarily always the case: I. Navarro, G. Fabrias, and F. Camps Angew. Chem., Int. Ed. 38 1999 164 166
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 164-166
    • Navarro, I.1    Fabrias, G.2    Camps, F.3
  • 41
    • 0000205069 scopus 로고
    • Although the work of Schuerch supports the notion of the 2-O-sulfonate group as a non-participating, disarming group in mannosylation and rhamnosylation, it is not clear to what extent the acetonitrile employed as solvent played a role in these reactions, as it is well known to have a strong β-directing effect: R.U. Lemieux, and R.M. Ratcliffe Can. J. Chem. 57 1979 1244 1251
    • (1979) Can. J. Chem. , vol.57 , pp. 1244-1251
    • Lemieux, R.U.1    Ratcliffe, R.M.2
  • 47
    • 4544334356 scopus 로고    scopus 로고
    • For a correction see: Angew. Chem., Int. Ed. 43 2004 4389
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 4389
  • 49
    • 0342475007 scopus 로고
    • The use of 2-O-nitrate esters in α-glucosylation has been described: M.L. Wolfrom, and K. Koizumi J. Org. Chem. 32 1967 656 660
    • (1967) J. Org. Chem. , vol.32 , pp. 656-660
    • Wolfrom, M.L.1    Koizumi, K.2
  • 51
    • 12344255133 scopus 로고
    • Nitrate esters are reported to be non-particpating in simple substitution reactions: L. Fishbein J. Am. Chem. Soc. 79 1957 2959 2962
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 2959-2962
    • Fishbein, L.1
  • 56
    • 0037070545 scopus 로고    scopus 로고
    • For applications of this chemistry in oligosaccharide synthesis see: D. Crich, and V. Dudkin J. Am. Chem. Soc. 124 2002 2263 2266
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 2263-2266
    • Crich, D.1    Dudkin, V.2
  • 68
  • 80
    • 0000252665 scopus 로고    scopus 로고
    • Fraser-Reid has explained the disarming effect of a 4,6-O-benzylidene acetal as arising from torsional strain encountered as the pyranose ring flattens to the sofa-conformation of the oxacarbenium ion, for which the term torsionally-disarming was coined: C.W. Andrews, R. Rodebaugh, and B. Fraser-Reid J. Org. Chem. 61 1996 5280 5289
    • (1996) J. Org. Chem. , vol.61 , pp. 5280-5289
    • Andrews, C.W.1    Rodebaugh, R.2    Fraser-Reid, B.3
  • 82
    • 3342978155 scopus 로고    scopus 로고
    • Very recently, Bols convincingly demonstrated that the disarming effect of the 4,6-O-benzylidene acetal arises in large part from the restriction of the C5-C6 bond to the tg conformation: H.H. Jensen, M. Nordstrom, and M. Bols J. Am. Chem. Soc. 126 2004 9205 9213
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 9205-9213
    • Jensen, H.H.1    Nordstrom, M.2    Bols, M.3
  • 90
    • 12344331724 scopus 로고    scopus 로고
    • note
    • The enhanced anomeric reactivity of deoxy sugars is well known and is summarized in Ref. 2c
  • 110
    • 12344270193 scopus 로고    scopus 로고
    • note
    • CH coupling values (in the region of 180-185 Hz for all anomeric fluorides)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.