A Tandem Ring-Closing Metathesis Cleavable Linker System for Solid-Phase Oligosaccharide Synthesis

Mattie S. M. Timmer; Jeroen D. C. Codée; Herman S. Overkleeft; Jacques H. van Boom; Gijsbert A. van der Marel

doi:10.1055/s-2004-831301

LETTER

A Tandem Ring-Closing Metathesis Cleavable Linker System for Solid-Phase Oligosaccharide Synthesis

Mattie S. M. Timmer, Jeroen D. C. Codée, Herman S. Overkleeft, Jacques H. van Boom^†, Gijsbert A. van der Marel*
Leiden Institute of Chemistry, Gorlaeus Laboratories, P. O. Box 9502, 2300 RA Leiden, The Netherlands
Fax: +31(071)5274307; e-Mail: g.marel@chem.leidenuniv.nl;

Abstract

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Abstract

A novel triene linker system, that can be cleaved by a tandem ring-closing metathesis (RCM) reaction, is presented. The tandem RCM cleavage, that regenerates the active ruthenium catalyst without the need of additives like ethylene, proceeded very clean and fast to liberate cyclopent-2-enyl mannosides from the solid support. A cyclopent-2-enyl mannoside was isomerized to the corresponding vinyl ether glycoside, which could be readily deprotected by iodine-mediated hydrolysis.

Key words

glycosylations - linker - metathesis - ruthenium - solid-phase

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References

These authors contributed equally to this work.

<A NAME="RG15004ST-2A">2a</A> Kanemitsu T. Kanie O. Trends Glycosci. Glyc. 1999, 11: 267

<A NAME="RG15004ST-2B">2b</A> Seeberger PH. Haase WC. Chem. Rev. 2000, 100: 4349

<A NAME="RG15004ST-2C">2c</A> Plante OJ. Palmacci ER. Seeberger PH. Science 2001, 291: 1523

<A NAME="RG15004ST-2D">2d</A> Sears P. Wong C.-H. Science 2001, 291: 2344

<A NAME="RG15004ST-2E">2e</A> Kanemitsu T. Kanie O. Comb. Chem. High Throughput Screening 2002, 5: 339

<A NAME="RG15004ST-2F">2f</A> Randell KD. Barkley A. Arya P. Comb. Chem. High Throughput Screening 2002, 5: 179

<A NAME="RG15004ST-2G">2g</A> Solid Support Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries Seeberger PH. Wiley; New York: 2001.

<A NAME="RG15004ST-2H">2h</A> Khersonsky SM. Ho CM. Garcia MAF. Chang YT. Curr. Top. Med. Chem. 2003, 3: 617

<A NAME="RG15004ST-2I">2i</A> Franzen R. Tois J. Comb. Chem. High Throughput Screening 2003, 6: 433

<A NAME="RG15004ST-2J">2j</A> Plante OJ. Seeberger PH. Curr. Opin. Drug Discovery Dev. 2003, 6: 521

<A NAME="RG15004ST-3A">3a</A> Gordon K. Balasubramanian S. J. Chem. Technol. Biotechnol. 1999, 74: 835

<A NAME="RG15004ST-3B">3b</A> Brown AR. Hermkens PHH. Ottenheijm HCJ. Rees DC. Synlett 1998, 817

<A NAME="RG15004ST-4A">4a</A> Ivin KJ. Mol JC. Olefin Metathesis and Olefin Metathesis Polymerization 1st ed.: Academic Press; London: 1997.

<A NAME="RG15004ST-4B">4b</A> Fürstner A. Top. Catal. 1997, 4: 285

<A NAME="RG15004ST-4C">4c</A> Schuster M. Blechert S. Angew. Chem., Int. Ed. Engl. 1997, 36: 2037

<A NAME="RG15004ST-4D">4d</A> Grubbs RH. Chang S. Tetrahedron 1998, 54: 4413

<A NAME="RG15004ST-4E">4e</A> Armstrong SK. J. Chem. Soc., Perkin Trans. 1 1998, 371

<A NAME="RG15004ST-4F">4f</A> Ivin KJ. J. Mol. Catal. A 1998, 133: 1

<A NAME="RG15004ST-4G">4g</A> Pandit UK. Overkleeft HS. Borer BC. Bieräugel H. Eur. J. Org. Chem. 1999, 959

<A NAME="RG15004ST-4H">4h</A> Wright DL. Curr. Org. Chem. 1999, 3: 211

<A NAME="RG15004ST-4I">4i</A> Blechert S. Pure Appl. Chem. 1999, 71: 1393

<A NAME="RG15004ST-4J">4j</A> Jørgensen P. Hadwiger P. Madsen R. Stütz AE. Wrodnigg TM. Curr. Org. Chem. 2000, 4: 565

<A NAME="RG15004ST-4K">4k</A> Roy R. Das SK. Chem. Commun. 2000, 519

<A NAME="RG15004ST-4L">4l</A> Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3013

<A NAME="RG15004ST-4M">4m</A> Hoveyda AH. Schrock RR. Chem.-Eur. J. 2001, 7: 945

<A NAME="RG15004ST-4N">4n</A> Schrock RR. Hoveyda AH. Angew. Chem. Int. Ed. 2003, 42: 4592

<A NAME="RG15004ST-4O">4o</A> Connon SJ. Blechert S. Angew. Chem. Int. Ed. 2003, 42: 1900

<A NAME="RG15004ST-4P">4p</A> Leeuwenburgh MA. Van der Marel GA. Overkleeft HS. Curr. Opin. Chem. Biol. 2003, 7: 757

<A NAME="RG15004ST-5A">5a</A> Knerr L. Schmidt RR. Synlett 1999, 1802

<A NAME="RG15004ST-5B">5b</A> Knerr L. Schmidt RR. Eur. J. Org. Chem. 2000, 2803

<A NAME="RG15004ST-5C">5c</A> Andrade RB. Plante OJ. Melean LG. Seeberger PH. Org. Lett. 1999, 1: 1811

<A NAME="RG15004ST-5D">5d</A> Melean LG. Haase WC. Seeberger PH. Tetrahedron Lett. 2000, 41: 4329

<A NAME="RG15004ST-5E">5e</A> Palmacci ER. Plante OJ. Hewitt MC. Seeberger PH. Helv. Chim. Acta 2003, 86: 3975

<A NAME="RG15004ST-5F">5f</A> Kanemitsu T. Seeberger PH. Org. Lett. 2003, 5: 4541

<A NAME="RG15004ST-6">6</A> Van Maarseveen JH. Den Hartog JAJ. Engelen V. Finner E. Visser G. Kruse CG. Tetrahedron 1993, 49: 3665

<A NAME="RG15004ST-7A">7a</A> Scholl M. Trnka TM. Morgan JP. Grubbs RH. Tetrahedron Lett. 1999, 40: 2247

<A NAME="RG15004ST-7B">7b</A> Trnka TM. Morgan JP. Sanford MS. Wilhelm TE. Scholl M. Choi TL. Ding S. Day MW. Grubbs RH. J. Am. Chem. Soc. 2003, 125: 2546

A combination of literature procedures was used:

<A NAME="RG15004ST-8A">8a</A> Nagarkatti JP. Ashley KR. Tetrahedron Lett. 1973, 14: 4599

<A NAME="RG15004ST-8B">8b</A> Hoye TR. Suhadolnik JC. Tetrahedron 1986, 42: 2855

<A NAME="RG15004ST-8C">8c</A> Meier H. Mayer W. Kolshorn H. Chem. Ber. 1987, 120: 685

<A NAME="RG15004ST-8D">8d</A> Ruan Z. Mootoo DR. Tetrahedron Lett. 1999, 40: 49

<A NAME="RG15004ST-8E">8e</A> Dabideen D. Ruan Z. Mootoo DR. Tetrahedron 2002, 58: 2077

<A NAME="RG15004ST-9">9</A> The loading was determined by spectroscopic analysis of a suspension of resin (2.0-3.0 mg) in 3% TCA in CH₂Cl₂ (50 mL): B = A₄₇₇·V/(εlm), where B = loading (mmol/g), A = absorbance at λ = 477 nm, V = volume (mL), ε = 56·10³ M^-1m^-1, l = pathway length (cm), m = mass of resin (g). See also: Will DW. Langner D. Knolle J. Uhlmann E. Tetrahedron 1995, 51: 12069

<A NAME="RG15004ST-10A">10a</A> Yamazaki F. Sato S. Nukada T. Ito Y. Ogawa T. Carbohydr. Res. 1990, 201: 31

<A NAME="RG15004ST-10B">10b</A> Paulsen H. Helpap B. Carbohydr. Res. 1991, 216: 289

<A NAME="RG15004ST-10C">10c</A> Mayer TG. Schmidt RR. Eur. J. Org. Chem. 1999, 1153