Practical synthesis of threo-(1S, 2S)- and erythro-(1R, 2S)-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol (PPMP) from L-serine

Synlett

Volumn , Issue 4, 1998, Pages 389-390

  Nishida, Atsushi ^a   Sorimachi, Hiroshi ^a   Iwaida, Mie ^a   Matsumizu, Miyako ^a   Kawate, Tomohiko ^a   Nakagawa, Masako ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000443556     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-3132     Document Type: Article

References (21)

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2. b) Inokuchi, J.-i.; Radin, N. S. J. Lipid Res. 1987, 28, 565-571;
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16. 1H-NMR technique was superior for determining the diastereomer ratio, as shown in Table 2. The stereochemistry of anti-3 was determined as reported elsewhere (ref. 5h). The structure of syn-3 was confirmed by X-ray crystallographic analysis.
17. Stereoselective reduction of structurally related ketones; a) Murakami, M.; Iwama, S.; Fujii, S.; Ikeda, K.; Katsumura. S. Bioorg. Med. Chem. Lett. 1997, 7, 1725-1728;
18. b) Doi, Y.; Ishibashi, M.; Kobayashi, J. Tetrahedron, 1996, 52, 4573-4580; and also ref. 5b.
19. The selectivity was reproducible when the reaction was carried out using 1 g of 5.
20. 2N-), 51.60 (C2), 36.78, 31.90, 29.65, 29.43, 29.30, 29.16, 25.65, 22.63, 13.98.
21. Racemic 1 (PPMP) and 2 (PDMP) are commercially available. Preparations of optically active 1 and 2 by separation of the four stereo isomers, which were obtained from non-stereoselective synthesis, were reported (ref. 1 and 1c).