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
Synthesis 2017; 49(18): 4299-4302
DOI: 10.1055/s-0036-1588857
DOI: 10.1055/s-0036-1588857
paper
Synthesis of l-Ribose from d-Ribose by a Stereoconversion through Sequential Lactonization as the Key Transformation
Further Information
Publication History
Received: 14 April 2017
Accepted after revision: 08 May 2017
Publication Date:
20 June 2017 (online)
‡ These authors contributed equally to this work.
Abstract
l-Ribose, a key precursor of various l-nucleosides can only be synthesized from other sugars or other non-sugar precursors. Herein, the study involves the synthesis of naturally rare l-ribose from readily available d-ribose. Though, many synthetic strategies are developed to meet the increasing demands of l-ribose, seeking innovation, a synthesis employing sequential lactonization as the key transformation was explored. This novel conversion involves protection, oxidation, sequential lactonization, reduction with DIBAL-H, and deprotection.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588857.
- Supporting Information
-
References
- 1 van Ekenstein WA. Blanksma J. Chem. Weekbl. 1909; 6: 373
- 2a Trimbur DE. Mortlock RP. J. Bacteriol. 1991; 173: 2459
- 2b Bailey JM. Biochem. Soc. Trans. 1997; 25: S651
- 3 Okano K. Tetrahedron 2009; 65: 1937
- 4 Cholongitas E. Vasiliadis T. Goulis I. Fouzas I. Antoniadis N. Papanikolaou V. Akriviadis E. J. Viral Hepatitis 2015; 22: 574
- 5 Anderson DL. Drugs Today 2009; 45: 331
- 6 Watson J. Curr. Opin. Invest. Drugs 2002; 3: 680
- 7 Reitsma JM. Terhune SS. Antiviral Res. 2013; 100: 321
- 8a Gunther WR. Duong Q. Roman-Leshkov YJ. Mol. Catal. A: Chem. 2013; 379: 294
- 8b Jeon YJ. Song SM. Lee CS. Kim IH. Hwahak Konghak 2011; 49: 628
- 8c Helanto M. Kiviharju K. Granstroem T. Leisola M. Nyyssoelae A. Appl. Microbiol. Biotechnol. 2009; 83: 77
- 8d Stephen JA. Aust. J. Chem. 2005; 58: 58
- 8e Bilik V. Caplovic J. Chem. Zvesti. 1973; 27: 547
- 9 Moyroud E. Strazewski P. Tetrahedron 1999; 55: 1277
- 10a Yun M. Moon HR. Kim HO. Choi WJ. Kim Y.-C. Park C.-S. Jeong LS. Tetrahedron Lett. 2005; 46: 5903
- 10b Kang J.-S. Yun M.-H. Lee S.-D. Jeon B.-C. Shin J.-A. Patent PCT Int. Appl. WO 2004007513, 2004
- 10c Sivets GG. Klennitskaya TV. Zhernosek EV. Mikhailopulo IA. Synthesis 2002; 253
- 10d Jung ME. Xu Y. Patent PCT Int. Appl. WO9839347, 1998
- 10e Jung ME. Xu Y. Tetrahedron Lett. 1997; 38: 4199
- 11 Seo MJ. An J. Shim JH. Kim G. Tetrahedron Lett. 2003; 44: 3051
- 12 Qi S. Zhang W. Feng Y. Tianranqi Huagong 2007; 32: 69
- 13 Shi Z.-D. Yang B.-H. Wu Y.-L. Tetrahedron 2002; 58: 3287
- 14 Perali RS. Mandava S. Bandi R. Tetrahedron 2011; 67: 4031
- 15a Wagner J. Vieira E. Vogel P. Helv. Chim. Acta 1988; 71: 624
- 15b Wulff G. Hansen A. Carbohydr. Res. 1987; 164: 123
- 15c Matteson DS. Peterson ML. J. Org. Chem. 1987; 52: 5116
- 15d Wulff G. Hansen A. Angew. Chem., Int. Ed. Engl. 1986; 25: 560
- 15e Yamaguchi M. Mukaiyama T. Chem. Lett. 1981; 1005
- 16 Takahashi H. Iwai Y. Hitomi Y. Ikegami S. Org. Lett. 2002; 4: 2401
- 17 Amorati R. Pedulli GF. Pratt DA. Valgimigli L. Chem. Commun. 2010; 46: 5139
- 18a Huang L. Teumelsan N. Huang X. Chem. Eur. J. 2006; 12: 5246
- 18b Bosch MP. Campos F. Niubó I. Rosell G. Díaz JL. Brea J. Loza MI. Guerrero A. J. Med. Chem. 2004; 47: 4041
- 19a Moreau C. Kirchberger T. Swarbrick JM. Bartlett SJ. Fliegert R. Yorgan T. Bauche A. Harneit A. Guse AH. Potter BV. L. J. Med. Chem. 2013; 56: 10079
- 19b Prabhakar P. Rajaram S. Reddy DK. Shekar V. Venkateswarlu Y. Tetrahedron: Asymmetry 2010; 21: 216
- 20 Zhao M. Li J. Mano E. Song Z. Tschaen DM. Grabowski EJ. J. Reider PJ. J. Org. Chem. 1999; 64: 2564
- 21 De Luca L. Giacomelli G. Masala S. Porcheddu A. J. Org. Chem. 2003; 68: 4999
- 22 Zanka A. Chem. Pharm. Bull. 2003; 51: 888
- 23 Lerner LM. Carbohydr. Res. 1988; 184: 250
- 24 CCDC 1446880 and CCDC 1446881 contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/get structures.
- 25 Punirun T. Soorukram D. Kuhakarn C. Reutrakul V. Pohmakotr M. J. Org. Chem. 2015; 80: 7946
- 26 Ivanova NA. Valiullina ZR. Shitikova OV. Miftakhov MS. Russ. J. Org. Chem. 2007; 43: 742
- 27a Huang L. Teumelsan N. Huang X. Chem. Eur. J. 2006; 12: 5246
- 27b Bosch MP. Campos F. Niubo I. Rosell G. Diaz JL. Brea J. Loza MI. Guerrero A. J. Med. Chem. 2004; 47: 4041
- 28 Attwood SV. Barrett AG. M. J. Chem. Soc., Perkin Trans. 1 1984; 1315
- 29 Matteson DS. Peterson ML. J. Org. Chem. 1987; 52: 5116