The thio-Mitsunobu reaction: A useful tool for the preparation of 2,5-anhydro-2-thio- and 3,5-anhydro-3-thiopentofuranosides

Carbohydrate Research

Volumn 339, Issue 10, 2004, Pages 1787-1802

  Schulze, Oliver ^a,b   Voss, Jürgen ^a   Adiwidjaja, Gunadi ^a   Olbrich, Falk ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

^b UNIVERSITY MEDICAL CENTER HAMBURG EPPENDORF   (Germany)

Author keywords

5 S Acetyl 5 thiopentofuranosides; Methyl 2,3 anhydro D ribofuranosides; Methyl 2,5 anhydro 2 thiopentofuranosides; Methyl 3,5 anhydro 3 seleno D lyxofuranoside; Methyl 3,5 anhydro 3 thiopentofuranosides; Thio Mitsunobu reaction

Indexed keywords

CARBONATES; HYDROGEN; SODIUM COMPOUNDS; STRUCTURE (COMPOSITION); X RAY DIFFRACTION ANALYSIS;

INTRAMOLECULAR NUCLEOPHILIC DISPLACEMENT; SODIUM HYDROGEN SELENIDE;

CARBOHYDRATES;

BICARBONATE; EPOXIDE; ETHYLENE OXIDE DERIVATIVE; FURAN DERIVATIVE; SELENIDE;

ARTICLE; CYCLIZATION; MITSUNOBU REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

ACETATES; ARABINOSE; BICARBONATES; BIOCHEMISTRY; CRYSTALLOGRAPHY, X-RAY; FURANS; HYDROGEN; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MODELS, MOLECULAR; SELENIUM COMPOUNDS; SODIUM; X-RAY DIFFRACTION; XYLOSE;

EID: 3042616193     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2004.04.020     Document Type: Article

References (33)

1. Mitsunobu O. Synthesis. 1981;1-28
2. Hughes D.L. Org. React. 42:1992;335-656
3. Kawai S.H., Chin J., Just G. Carbohydr. Res. 211:1991;245-260
4. Dancy I., Laupichler L., Rollin P., Thiem J. Liebigs Ann. Chem. 1993;343-350
5. Brånalt J., Kvarnström I., Classon B., Samuelsson J. J. Org. Chem. 61:1996;3604-3610
6. Moravková J., Rollin P., Lorin C., Gardon V., Č apková J., Mazáč J. J. Carbohydr. Chem. 16:1997;113-127
7. Schulze O., Voss J., Adiwidjaja G. Synthesis. 2001;229-234
8. Adiwidjaja G., Brunck J.-S., Polchow K., Voss J. Carbohydr. Res. 325:2000;237-244
9. Schulze O., Bruns S., Voss J., Adiwidjaja G. Carbohydr. Res. 329:2000;781-790
10. Preliminary note: Voss J., Schulze O., Olbrich F., Adiwidjaja G. Phosphorus Sulfur Silicon. 120-121:1997;389-390
11. Yuasa H., Kajimoto T., Wong C.-H. Tetrahedron Lett. 35:1994;8243-8246
12. Yuasa H., Hashimoto H. Rev. Heteroat. Chem. 19:1998;35-65
13. Bozó É., Boros S., Kuczmann J. Carbohydr. Res. 329:2000;525-528
14. Hirota K., Kitade Y., Tomishi T., Maki Y., De Clercq E. J. Chem. Soc., Perkin Trans. 1. 1988;2233-2241
15. Yoshimura Y., Kitano K., Yamada K., Satoh H., Watanabe M., Miura S., Sakata S., Sasaki T., Matsuda A. J. Org. Chem. 62:1997;3140-3152
16. Singh S.K., Kumar R., Wengel J. J. Org. Chem. 63:1998;6078-6079
17. Yoshikawa M., Murakami T., Shimada H., Matsuda H., Yamahara J., Tanabe G., Muraoka O. Tetrahedron Lett. 38:1997;8367-8370
18. Yuasa H., Takada J., Hashimoto H. Tetrahedron Lett. 41:2000;6615-6618
19. Ghavami A., Johnston B.D., Pinto B.M. J. Org. Chem. 66:2001;2312-2317
20. Wirsching, J. Ph.D. thesis, University of Hamburg, 2000, to be published elsewhere
21. Collins P., Ferrier R. Monosaccharides. Their Chemistry and Their Roles in Natural Products. 1995;Wiley, Chichester. pp 194-196
22. Lehmann J. Kohlenhydrate. Chemie und Biologie. 2nd ed. 1996;Thieme, Stuttgart, New York. pp 115-116
23. Miljkovic M., Gligorijewic M., Glišin D. J. Org. Chem. 39:1974;3223-3226
24. Richardson A.C. Carbohydr. Res. 10:1969;395-402. and references cited therein
25. Fernandez-Bolaños J.G., Al-Masoudi N.A.L., Maya I. Adv. Carbohydr. Chem. Biochem. 57:2001;21-98. and references cited therein
26. Bozó É., Medgyes A., Boros S., Kuczmann J. Carbohydr. Res. 329:2000;25-40. and references cited therein
27. Thomé M.A., Giudicelli M.B., Picq D., Anker D. J. Carbohydr. Chem. 10:1991;923-926
28. Adiwidjaja G., Schulze O., Voss J., Wirsching J. Carbohydr. Res. 325:2000;107-119
29. Becker H. Organikum: Organisch-chemisches Grundpraktikum. 19th ed. 1993;Johann Ambrosius Barth, Leipzig. pp 659-681
30. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Burla, M. C.; Polidori, G.; Camalli, M.; Spagna, R. SIR97; A Package for Crystal Structure Solution by Direct Methods and Refinement, Bari, Perugia, Rome, Italy, 1997
31. Sheldrick, G. M. SHELXL-97; Program for Crystal Structure Refinement, University of Göttingen, Göttingen, Germany, 1997
32. Spek, A. L. PLATON; A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, 1999
33. Baker B.R., Schaub R.E., Williams J.H. J. Am. Chem. Soc. 77:1955;7-12