Solid phase synthesis of mandelic acid-derived thioethers by α-keto carbocation trapping

Tetrahedron Letters

Volumn 45, Issue 7, 2004, Pages 1381-1383

  Fruchart, Jean Sébastien ^a   Behr, Jean Bernard ^b   Melnyk, Oleg ^a  

^a INSTITUT DE BIOLOGIE DE LILLE   (France)

^b CNRS   (France)

Author keywords

Mandelic acid; Solid phase; Thioethers; Keto carbocation

Indexed keywords

MANDELIC ACID; SULFIDE; THIOL DERIVATIVE;

ACIDITY; ARTICLE; CHEMICAL REACTION; SOLID; STANDARDIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 1642497634     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.062     Document Type: Article

References (10)

1. Mühlman A., Classon B., Hallberg A., Samuelsson B. J. Med. Chem. 44:2001;3402.
2. Otera J., Nakazawa K., Segokuchi K., Orita A. Tetrahedron. 53:1997;13633.
3. Chan W.C., White P.D. Fmoc Solid-Phase Peptide Synthesis, A Practical Approach. 2000;Oxford University Press, Oxford.
4. 2/anisole/water (45/45/5/5 by volume) to liberate 1a and generate 4 from the residual mesylate. RP-HPLC analysis was performed after evaporation of the crude mixture. Conversion was deduced from relative integration of the corresponding peaks.
5. 2/RSH gave alcohol 4 as the only reaction product.
6. 2 (1 mL), TFA (1 mL) and RSH (100 μL or 10 equiv). After 30 min of stirring, the resin was filtered and washed twice with TFA (1 mL). The combined filtrates were co-evaporated twice with heptane (15 mL). The crude residue was purified by preparative RP-HPLC or flash chromatography on silica gel (see Table 1).
7. 3COOD.
8. Creary X., Geiger C.C. J. Am. Chem. Soc. 104:1982;4151.
9. Creary X., McDonald S.R., Eggers M.D. Tetrahedron Lett. 26:1985;811.
10. 3, DEAD) failed.