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Volumn 75, Issue 12, 2010, Pages 4284-4287

Stereoselective synthesis of β-Phenylselenoglycosides from glycals and rationalization of the selenoglycosylation processes

Author keywords

[No Author keywords available]

Indexed keywords

BENZENESELENOL; GLYCALS; RING OPENING; STEREOSELECTIVE SYNTHESIS;

EID: 77953532949     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100145s     Document Type: Article
Times cited : (17)

References (50)
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    • For a comprehensive review on selenium-containing sugars see
    • For a comprehensive review on selenium-containing sugars see: Witczak, Z. J.; Czernecki, S. Adv. Carbohydr. Chem. Biochem. 1998, 53, 143
    • (1998) Adv. Carbohydr. Chem. Biochem. , vol.53 , pp. 143
    • Witczak, Z.J.1    Czernecki, S.2
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    • For early synthetic approaches to selenoglycosides see
    • For early synthetic approaches to selenoglycosides see: Schneider, W.; Wrede, F. Ber. Dtsch. Chem. Ges. 1917, 50, 793
    • (1917) Ber. Dtsch. Chem. Ges. , vol.50 , pp. 793
    • Schneider, W.1    Wrede, F.2
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    • 2 is not used as the promoting Lewis acid to open epoxide 2 synthetized with Murrays reagent DMDO (for DMDO preparation see: Murray, R.W.; Singh, M. Org. Synth. 1997, 74, 91)
    • 2 is not used as the promoting Lewis acid to open epoxide 2 synthetized with Murrays reagent DMDO (for DMDO preparation see: Murray, R.W.; Singh, M. Org. Synth. 1997, 74, 91)
    • (1990) Carbohydr. Res. , vol.206 , pp. 361
    • Gordon, D.M.1    Danishefsky, S.J.2
  • 24
    • 0014443774 scopus 로고
    • For pioneering studies on ring opening of 1,2-anhydropyranoside (Brigl anhydride) with benzeneselenol, see:;;, and ref 1h
    • For pioneering studies on ring opening of 1,2-anhydropyranoside (Brigl anhydride) with benzeneselenol, see: Frenzel, H.; Nuhn, P.; Wagner, G. Arch. Pharm. 1962, 302, 62 and ref 1h.
    • (1962) Arch. Pharm. , vol.302 , pp. 62
    • Frenzel, H.1    Nuhn, P.2    Wagner, G.3
  • 30
    • 20144370684 scopus 로고    scopus 로고
    • references cited therein. Except for 5 and conformationally similar 3,4-di- O- TBDS- or 3,4-di- O -TIPS- d -glucal, other β- phenylselenoglycosides were prepared by the authors in a different way
    • Terauchi, M.; Yahiro, Y.; Abe, H.; Ichikawa, S.; Tovey, S. C.; Dedos, S. G.; Taylor, C. W.; Potter, B. V. L.; Matsuda, A.; Shuto, S. Tetrahedron 2005, 61, 3697 and references cited therein. Except for 5 and conformationally similar 3,4-di- O- TBDS- or 3,4-di- O -TIPS- d -glucal, other β- phenylselenoglycosides were prepared by the authors in a different way
    • (2005) Tetrahedron , vol.61 , pp. 3697
    • Terauchi, M.1    Yahiro, Y.2    Abe, H.3    Ichikawa, S.4    Tovey, S.C.5    Dedos, S.G.6    Taylor, C.W.7    Potter, B.V.L.8    Matsuda, A.9    Shuto, S.10
  • 34
    • 77953511154 scopus 로고    scopus 로고
    • We found that when using PhSeH as the nucleophile in the direct oxidative glycosylation with glucal 6, Lewis acid is not necessary for coupling to proceed
    • We found that when using PhSeH as the nucleophile in the direct oxidative glycosylation with glucal 6, Lewis acid is not necessary for coupling to proceed.
  • 36
    • 0001443980 scopus 로고
    • For examples of α-approach of electrophilic reagents onto the C(2) position of protected glycals see
    • For examples of α-approach of electrophilic reagents onto the C(2) position of protected glycals see: Grewal, G.; Kaila, N.; Franck, R. W. J. Org. Chem. 1992, 57, 2084
    • (1992) J. Org. Chem. , vol.57 , pp. 2084
    • Grewal, G.1    Kaila, N.2    Franck, R.W.3
  • 38
    • 77953515895 scopus 로고    scopus 로고
    • Traces (less than 5%) of the corresponding formate, inseparable from the glycosylation product, are also obtained in the β-phenylselenoglycosylation of glucal 6. Control reaction carried out on β-phenylselenoglycoside 13 and α-phenylselenoglycoside 22, independently synthetized by ring opening of epoxy galactal 21 (see ref 13) with PhSeH, showed the stability of both glycosides to the Gins reaction conditions with no evident isomerization to formate 15. Investigations into the validity of the proposed reaction pathway proposed for the formation of 15 are currently underway
    • Traces (less than 5%) of the corresponding formate, inseparable from the glycosylation product, are also obtained in the β-phenylselenoglycosylation of glucal 6. Control reaction carried out on β-phenylselenoglycoside 13 and α-phenylselenoglycoside 22, independently synthetized by ring opening of epoxy galactal 21 (see ref 13) with PhSeH, showed the stability of both glycosides to the Gins reaction conditions with no evident isomerization to formate 15. Investigations into the validity of the proposed reaction pathway proposed for the formation of 15 are currently underway.
  • 42
    • 77953482408 scopus 로고    scopus 로고
    • The isomerization from the less carbocationic 24 to the more carbocationic intermediate 25 is favored by the ability of the endocyclic oxygen to stabilize, by conjugative electron-donating effect, the developing of an adjacent carbocationic center
    • The isomerization from the less carbocationic 24 to the more carbocationic intermediate 25 is favored by the ability of the endocyclic oxygen to stabilize, by conjugative electron-donating effect, the developing of an adjacent carbocationic center.
  • 43
    • 0034710476 scopus 로고    scopus 로고
    • For examples of cis opening of glycal epoxides metal-catalyzed see
    • For examples of cis opening of glycal epoxides metal-catalyzed see: Rainier, J. D.; Cox, J. M. Org. Lett. 2000, 2, 2707
    • (2000) Org. Lett. , vol.2 , pp. 2707
    • Rainier, J.D.1    Cox, J.M.2
  • 48
    • 77953483793 scopus 로고    scopus 로고
    • + also affords only β-selenoglycoside 13 and β-selenoglycoside 12, respectively
    • + also affords only β-selenoglycoside 13 and β-selenoglycoside 12, respectively.
  • 49
    • 0032568331 scopus 로고    scopus 로고
    • 2 was found to be not able to determine the formation of a fully developed carbocationic species. See refs 9 and 14, as well as the following
    • 2 was found to be not able to determine the formation of a fully developed carbocationic species. See refs 9 and 14, as well as the following: Evans, D. A.; Trotter, B. W.; Côté, B. Tetrahedron Lett. 1998, 39, 1709
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1709
    • Evans, D.A.1    Trotter, B.W.2    Côté, B.3
  • 50
    • 77953533651 scopus 로고    scopus 로고
    • 2 (2 equiv) did not lead to anomeric epimerization after 24 h at 23 °C
    • 2 (2 equiv) did not lead to anomeric epimerization after 24 h at 23 °C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.