First asymmetric synthesis of chiral analogues of the novel immunosuppressant FTY720

Tetrahedron Letters

Volumn 43, Issue 45, 2002, Pages 8095-8097

  Hinterding, Klaus ^a   Albert, Rainer ^a   Cottens, Sylvain ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

FTY720; Immunosuppressant; Phosphates; Schoellkopf auxiliary

Indexed keywords

FINGOLIMOD; PHOSPHATE;

ARTICLE; CHIRALITY; DRUG MECHANISM; DRUG SYNTHESIS; ENANTIOMER; HYDROLYSIS; PHYSICAL CHEMISTRY; STEREOCHEMISTRY;

ANIMALIA;

EID: 0037020584     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01925-1     Document Type: Article

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11. The diastereomeric ratio (>10:1) of this step was irrelevant, since the stereochemical outcome of the overall sequence was determined by the following methylation.
12. 4. After evaporation of the solvent the crude oil was purified by chromatography (hexanes/ether=9/1) to give the desired product as a slowly crystallizing oil (9.87 g, 22.2 mmol).
13. 3).
14. Alternatively, bis-alkylated Schöllkopf adducts 7 can be synthesized from L-cyclo-Val-Ala-OMe by alkylation with iodide 6.
15. Column: Chiracel OD (25×0.46 cm); Eluent: EtOH/hexane=1/1; UV detection at 210 nm; flow: 1 ml/min; injection: 20 mL 0.1% in EtOH; ee of (R)-3=95%.
16. 2/THF.
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18. -.