Efficient and Practical Synthesis
of 5′-Deoxytubercidin and Its Analogues via Vorbrüggen
Glycosylation

Yang Song; Haixin Ding; Yanhui Dou; Ruchun Yang; Qi Sun; Qiang Xiao; Yong Ju

doi:10.1055/s-0030-1259975

PAPER

Efficient and Practical Synthesis of 5′-Deoxytubercidin and Its Analogues via Vorbrüggen Glycosylation

Yang Song^a, Haixin Ding^b, Yanhui Dou^b, Ruchun Yang^b, Qi Sun^b, Qiang Xiao*^b, Yong Ju*^a
^a Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
Fax: +86(10)62781695; e-Mail: juyong@tsinghua.edu.cn ;
^b Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, P. R. of China
Fax: +86(791)6422903; e-Mail: xiaoqiang@tsinghua.org.cn ;

Abstract

Alle Artikel dieser Rubrik

Abstract

An efficient and practical synthesis of naturally occurring marine nucleosides 5′-deoxytubercidins on a 10 gram scale in good overall yield is reported. The key step was the Vorbrüggen glycosylation of pyrrolo[2,3-d]pyrimidines with 5-deoxy-1,2,3-tri-O-acetyl-β-d-ribofuranose.

Key words

5′-deoxytubercidin - Vorbrüggen glycosylation - pyrrolo[2,3-d]pyrimidine - marine nucleoside - 7-deazapurine

Volltext

Referenzen

References

<A NAME="RF14911SS-1">1</A> Sagar S. Kaur M. Minneman KP. Mar. Drugs 2010, 8: 2619

<A NAME="RF14911SS-2A">2a</A> Seela F. Peng XH. Curr. Top. Med. Chem. 2006, 6: 867

<A NAME="RF14911SS-2B">2b</A> Seela F. Peng XH. Budow S. Curr. Org. Chem. 2007, 11: 427

<A NAME="RF14911SS-2C">2c</A> Taylor EC. Kuhnt D. Shih C. Rinzel SM. Grindey GB. Barredo J. Jannatipour M. Moran RG. J. Med. Chem. 1992, 35: 4450

<A NAME="RF14911SS-3">3</A> Changelian PS. Flanagan ME. Ball D. Kent CR. Borie DC. Science 2003, 302: 875

<A NAME="RF14911SS-4A">4a</A> Nakamura G. J. Antibiot. 1961, 14A: 90

<A NAME="RF14911SS-4B">4b</A> Nishimura H. Katagiri K. Sato K. Mayama M. Shimaoka NT. J. Antibiot. 1956, 9A: 60

<A NAME="RF14911SS-4C">4c</A> Ohkuma K. J. Antibiot. 1961, 14A: 343

<A NAME="RF14911SS-5">5</A> Kazlauskas R. Murphy PT. Wells RJ. Baird-Lambert JA. Jamieson DD. Aust. J. Chem. 1983, 36: 165

<A NAME="RF14911SS-6">6</A> Mitchell SS. Pomerantz SC. Concepción GP. Ireland CM. J. Nat. Prod. 1996, 59: 1000

<A NAME="RF14911SS-7">7</A> Cook AF. Holman MJ. Nucleosides Nucleotides 1984, 4: 401

<A NAME="RF14911SS-8A">8a</A> Phillis JW. Smith-Barbour M. Life Sci. 1993, 53: 497

<A NAME="RF14911SS-8B">8b</A> Davies LP. Cook AF. Life Sci. 1995, 56: PL345

<A NAME="RF14911SS-8C">8c</A> Ugarkar BG. DaRe JM. Kopcho JJ. Browne CE. Schanzer JM. Wiesner JB. Erion MD. J. Med. Chem. 2000, 43: 2883

<A NAME="RF14911SS-9A">9a</A> Kazimierczuk Z. Revankar GR. Robins RK. Nucleic Acids Res. 1984, 12: 1179

<A NAME="RF14911SS-9B">9b</A> Ramasamy K. Imamura N. Robins RK. Revankar GR. Tetrahedron Lett. 1987, 28: 5107

<A NAME="RF14911SS-9C">9c</A> Ramasamy K. Imamura N. Robins RK. Revankar GR. J. Heterocycl. Chem. 1988, 25: 1893

<A NAME="RF14911SS-10A">10a</A> Lüpke U. Seela F. Chem. Ber. 1979, 112: 3526

<A NAME="RF14911SS-10B">10b</A> Seela F. Muth H.-P. Bindig U. Synthesis 1988, 670

<A NAME="RF14911SS-10C">10c</A> Seela F. Westermann B. Bindig U. J. Chem. Soc., Perkin Trans. 1 1988, 697

<A NAME="RF14911SS-10D">10d</A> Rosemeyer H. Seela F. Helv. Chim. Acta 1988, 71: 1573

<A NAME="RF14911SS-10E">10e</A> Seela F. Kretschmer U. J. Heterocycl. Chem. 1990, 27: 479

<A NAME="RF14911SS-10F">10f</A> Seela F. Soulimane T. Mersmann K. Jürgens T. Helv. Chim. Acta 1990, 73: 1879

<A NAME="RF14911SS-11A">11a</A> Ugarkar BG. Castellino AJ. DaRe JM. Kopcho JJ. Schanzer JM. Erion MD. J. Med. Chem. 2000, 43: 2894

<A NAME="RF14911SS-11B">11b</A> Ugarkar BG. Castellino AJ. DaRe JM. Ramirez-Weinhouse M. Kopcho JJ. Rosengren S. Erion MD. J. Med. Chem. 2003, 46: 4750

<A NAME="RF14911SS-12A">12a</A> Kane PD. Mann J. J. Chem. Soc., Perkin Trans. 1 1984, 657

<A NAME="RF14911SS-12B">12b</A> Wilcox CS. Otoski RM. Tetrahedron Lett. 1986, 27: 1011

<A NAME="RF14911SS-12C">12c</A> Sanghvi YS. Larson SB. Willis RC. Robins RK. Revankar GR. J. Med. Chem. 1989, 32: 945

<A NAME="RF14911SS-13A">13a</A> Niedballa U. Vorbruggen H. J. Org. Chem. 1976, 41: 2084

<A NAME="RF14911SS-13B">13b</A> Vorbruggen H. Krolikiewicz K. Bennua B. Chem. Ber. 1981, 114: 1234

<A NAME="RF14911SS-13C">13c</A> Teng K. Cook PD. J. Org. Chem. 1994, 59: 278

<A NAME="RF14911SS-13D">13d</A> Zhong MH. Robins MJ. Tetrahedron Lett. 2003, 44: 9327

<A NAME="RF14911SS-13E">13e</A> Spadafora M. Mehiri M. Burger A. Benhida R. Tetrahedron Lett. 2008, 49: 3967

<A NAME="RF14911SS-13F">13f</A> Vorbrüggen H. Ruh-Pohlenz C. Handbook of Nucleoside Synthesis Wiley; New York: 2001.

<A NAME="RF14911SS-14A">14a</A> Sharma M. Bloch A. Bobek M. Nucleosides Nucleotides 1993, 12: 643

<A NAME="RF14911SS-14B">14b</A> Sharma M. Li YX. Ledvina M. Bobek M. Nucleosides Nucleotides 1995, 14: 1831

<A NAME="RF14911SS-14C">14c</A> Porcari AR. Townsend LB. Nucleosides Nucleotides 1999, 18: 153

<A NAME="RF14911SS-14D">14d</A> Gunic E. Girardet J.-L. Pietrzkowski Z. Esler C. Wang G. Bioorg. Med. Chem. 2001, 9: 163

<A NAME="RF14911SS-14E">14e</A> Smith KL. Lai VCH. Prigaro BJ. Ding YL. Gunic E. Girardet J.-L. Zhong WD. Hong Z. Lang S. An HY. Bioorg. Med. Chem. Lett. 2004, 14: 3517

<A NAME="RF14911SS-15A">15a</A> Seela F. Peng XH. J. Org. Chem. 2006, 71: 81

<A NAME="RF14911SS-15B">15b</A> Seela F. Ming X. Tetrahedron 2007, 63: 9850

<A NAME="RF14911SS-15C">15c</A> Peng XH. Seela F. Nucleosides, Nucleotides Nucleic Acids 2007, 26: 603

<A NAME="RF14911SS-16A">16a</A> Dillon MP, Bois DJD, Lai YJ, Hawley RC, and Wang BH. inventors; PCT Int. Appl. WO 2010066629. ; Chem. Abstr. 2010, 153, 37183

<A NAME="RF14911SS-16B">16b</A> Nichols PL, Sehmi SS, Ward RW, and Wilson DM. inventors; PCT Int. Appl. WO 2009080682. ; Chem. Abstr. 2009, 151, 124018

<A NAME="RF14911SS-17">17</A> Wang CJ, and Tang DL. inventors; Faming Zhuanli Shenqing Gongkai Shuomingshu, WO2008092405. ; Chem. Abstr. 2007, 147, 301387

<A NAME="RF14911SS-18">18</A> Bio MM. Xu F. Waters M. Williams JM. Savary KA. Cowden CJ. Yang C. Buck E. Song ZJ. Tschaen DM. Volante RP. Reamer RA. Grabowski EJJ. J. Org. Chem. 2004, 69: 6257

<A NAME="RF14911SS-19A">19a</A> Tolman RL. Robins RK. Townsend LB. J. Am. Chem. Soc. 1968, 90: 524

<A NAME="RF14911SS-19B">19b</A> Tolman RL. Robins RK. Townsend LB. J. Am. Chem. Soc. 1969, 91: 2102

<A NAME="RF14911SS-19C">19c</A> Wang GY. Tam RC. Gunic E. Du JF. Bard J. Pai B. J. Med. Chem. 2000, 43: 2566

Zusatzmaterial

Supporting Information (PDF) (opens in new window)