Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2005(6): 939-944
DOI: 10.1055/s-2005-861828
DOI: 10.1055/s-2005-861828
PAPER
© Georg Thieme Verlag Stuttgart · New YorkNew Synthesis of Mannoside-Containing Neoglycoconjugates by Reaction of Propargyl Mannosides with Polyalkylcarboxylated Scaffolds
Further Information
Received
24 September 2004
Publication Date:
21 February 2005 (online)
Publication History
Publication Date:
21 February 2005 (online)
Abstract
A new, efficient and easy synthesis of multivalent mannoside neoglyconjugates is described by the alkynylation reaction of lithium acetylides derived from adequately protected propargyl α-d-mannoside and readily available polyalkylcarboxylate benzene derivatives as scaffolds.
Key words
glycosides - neoglycoconjugates - clusters - alkynes - polyalkylcarboxylates
- 1a
Varki A. Glycobiology 1993, 3: 97 - 1b Essentials of Glycobiology Cold Spring Harbor Laboratory Press; Cold Spring Harbor, New York: 1999.
- 1c
Dwek RA. Chem. Rev. 1996, 96: 683 - 1d
Blass BE.Coburn KR.Faulkner AL.Hunn CL.Natchus MG.Parker MS.Portlock DE.Tullis JS.Wood R. Tetrahedron Lett. 2002, 43: 4059 - 1e
Lis H.Sharon N. Chem. Rev. 1998, 98: 637 - 2a
Kiessling LL.Gestwicki JE.Strong LE. Curr. Opin. Chem. Biol. 2000, 4: 696 - 2b
Roy R. Curr. Opin. Struct. Biol. 1996, 6: 692 - 2c
Mammen M.Choi SK.Whitesides GM. Angew. Chem. Int. Ed. 1998, 37: 2755 - 3a Neoglycoconjugates. Preparations and Applications Academic Press, Inc.; San Diego: 1994.
- 3b
Davis BG. J. Chem. Soc., Perkin Trans. 1 1999, 3215 - 4a
Lee RT.Lee YC. In NeoglycoconjugatesLee YC.Lee RT. Academic Press; San Diego: 1994. p.23 - 4b
Lee YC.Lee RT. Acc. Chem. Res. 1995, 28: 321 - 4c
Lee RT.Lee YC. Glycoconjugate J. 2000, 17: 543 - 4d
Lundquist JJ.Toone EJ. Chem. Rev. 2002, 102: 555 - 5
Drickamer K.Taylor ME. Annu. Rev .Cell Biol. 1993, 9: 237 - 6
Ashwell G.Harford J. Annu. Rev. Biochem. 1982, 51: 531 - 7a
Sharon N.Lis H. Science 1989, 246: 227 - 7b
Sharon N. FEBS Lett. 1987, 217: 145 - 8a
Lindhorst TK.Kotter S.Kubisch J.Krallmannwenzel U.Ehlers S.Kren V. Eur. J. Org. Chem. 1998, 1669 - 8b
Kotter S.Krallmannwenzel U.Ehlers S.Lindhorst TK. J. Chem. Soc., Perkin Trans. 1 1998, 2193 - 8c
Lindhorst TK.Dubber M.Krallmann-Wenzel U.Ehlers S. Eur. J. Org. Chem. 2000, 2027 - 8d
Dubber M.Lindhorst TK. J. Org. Chem. 2000, 65: 5275 - 8e
Lindhorst TK.Kötter S.Krallmann-Wenzel U.Ehlers S. J. Chem. Soc., Perkin Trans. 1 2001, 823 - 8f
Dubber M.Lindhorst TK. Synthesis 2001, 327 - 8g
Rockendorf N.Sperling O.Lindhorst TK. Aust. J. Chem. 2002, 55: 87 - 8h
García-López JJ.Hernández-Mateo F.Isac-García J.Kim JM.Roy R.Santoyo-González F. J. Org. Chem. 1999, 64: 522 - 8i
García-López JJ.Santoyo-González F.Vargas-Berenguel A.Gimenez-Martinez JJ. Chem.-Eur. J. 1999, 5: 1775 - 8j
Roy R.Das SK.Santoyo-González F.Hernández-Mateo F.Dam TK.Brewer CF. Chem.-Eur. J. 2000, 6: 1757 - 8k
Roy R.Das SK.Hernandez-Mateo F.Santoyo-Gonzalez F.Gan ZH. Synthesis 2001, 1049 - 8l
Ortega-Caballero F.Giménez-Martínez JJ.Vargas-Berenguel A. Org. Lett. 2003, 5: 2389 - 8m
Perez-Balderas F.Ortega-Muñoz M.Morales-Sanfrutos J.Hernández-Mateo F.Calvo-Flores FG.Calvo-Asín JA.Isac-García J.Santoyo-González F. Org. Lett. 2003, 5: 1951 - 8n
Langer P.Ince SJ.Ley SV. J. Chem. Soc., Perkin Trans. 1 1998, 3913 - 8o
Dimick SM.Powell SC.McMahon SA.Moothoo DN.Naismith JH.Toone EJ. J. Am. Chem. Soc. 1999, 121: 10286 - 8p
Corbell JB.Lundquist JJ.Toone EJ. Tetrahedron: Assymmetry 2000, 11: 95 - 8q
Burke ST.Zhao Q.Shuster MC.Kiessling LL. J. Am. Chem. Soc. 2000, 122: 4518 - 8r
Grandjean C.Rommens C.Gras-Masse H.Melnyk O. Angew. Chem. Int. Ed. 2000, 39: 1068 - 8s
Hasegawa T.Yonemura T.Matsuura K.Kobayashi K. Tetrahedron Lett. 2001, 42: 3989 - 8t
Fulton DA.Stoddart JF. Bioconjugate Chem. 2001, 12: 655 - 8u
Baussanne I.Benito JM.Mellet CO.Fernandez JMG.Defaye J. ChemBioChem 2001, 2: 777 - 8v
Mellet CO.Defaye J.Fernandez JMG. Chem.-Eur. J. 2002, 8: 1982 - 9a
Gan ZH.Roy R. Tetrahedron Lett. 2000, 41: 1155 - 9b
Liu B.Roy R. J. Chem. Soc., Perkin Trans.1 2001, 773 - 10a
Perez-Balderas F.Santoyo-González F. Synlett 2001, 1699 - 10b
Dondoni A.Marra A.Zampolli MG. Synlett 2002, 1850 - 10c
Liu B.Roy R. Chem. Commun. 2002, 594 - 10d
Gan Z.Roy R. Can. J. Chem. 2002, 80: 908 - 10e
Andre S.Liu B.Gabius HJ.Roy R. Org. Biomol. Chem. 2003, 1: 3909 - 10f
Liu B.Roy R. Tetrahedron 2001, 57: 6909 - 10g
Sengupta S.Sadhukhan SK. Carbohydr. Res. 2001, 332: 215 - 11a
Kaufman RJ.Sidhu RS. J. Org. Chem. 1982, 47: 4941 - 11b
Dominique R.Liu B.Das SK.Roy R. Synthesis 2000, 862 - 12a For general treaties on nucleophilic additions to unsaturated systems see: Comprehensive Organic Synthesis
Vol. 1:
Trost B.Fleming I. Pergamon Press; New York: 1991. - 12b See also: Comprehensive Organic Synthesis
Vol. 1 Vol. 2:
Trost B.Fleming I. Pergamon Press; New York: 1991. - 12c For a recent report on the addition of alkynyl organometallic reagents to carbonyl
compounds see:
Tzalis D.Knochel P. Angew. Chem. Int. Ed. 1999, 38: 1463 - 12d
Jiang B.Si YG. Tetrahedron Lett. 2002, 43: 8323 - 12e See also:
Jiang B.Chen Z.Tang X. Org. Lett. 2002, 4: 3451 - 12f See also:
Lu G.Li X.Chen G.Chan WL.Chan ASC. Tetrahedron: Asymmetry 2003, 14: 449 - 12g See also:
Ishikawa T.Mizuta T.Hagiwara K.Aikawa T.Kudo T.Saito S. J. Org. Chem. 2003, 68: 3702 - 13a
Hess K.Weltzien W. Ber. 1921, 54B: 2511 - 13b
Rossander SS.Marvel CS. J. Am. Chem. Soc. 1929, 51: 932 - 14
Komatsu K.Takai T.Aonuma S.Takeuchi K. Tetrahedron Lett. 1988, 29: 5157 - 15
Church NJ.Young DW. J. Chem. Soc., Perkin Trans. 1 1998, 1475 - 16
Baldwin JE.Spivey AC.Schofield CJ.Sweeney JB. Tetrahedron 1993, 49: 6309 - 17a
Ohmori K.Suzuki T.Taya K.Tanabe D.Ohta T.Suzuki K. Org. Lett. 2001, 3: 1057 - 17b
Ohmori K.Hachisu Y.Suzuki T.Suzuki K. Tetrahedron Lett. 2002, 43: 1031 - 18
Tykwinski RR.Diederich F.Gramlich V.Seiler P. Helv. Chim. Acta 1996, 79: 645 - 19
Bezouska K. Rev. Mol. Biotech. 2002, 90: 290 - 20
Mereyala HB.Gurrala SR. Carbohydr. Res. 1998, 307: 351 - 21
Zhu Z.Espenson JH. J. Am. Chem. Soc. 1996, 118: 9901 - 22
Martier J.Vaultier M.Carreaux F.Donin J.-C. J. Org. Chem. 1998, 63: 3515 - 23
Kim JM.Roy R. Carbohydr. Res. 1997, 298: 173
References
2-Propynyl α-d-mannopyranoside was synthesized from per-O-acetyl α-d-mannopyranoside and propargyl alcohol following the procedure described by Mereyala et al. [20]