A remarkably simple process for monoprotecting diols

Tetrahedron Letters

Volumn 37, Issue 5, 1996, Pages 625-628

  Houille, Olivier ^a   Schmittberger, Thierry ^a   Uguen, Daniel ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYACID; TRIACYLGLYCEROL LIPASE;

ARTICLE; ENANTIOMER; ENZYME ACTIVITY; HYDROLYSIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030065709     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02273-2     Document Type: Article

References (28)

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7. a) Adjé, N.; Brouilles, P.; Uguen, D. Tetrahedron Lett. 1993, 34, 4631-4634, note 4; Takasu, M.; Naruse, Y.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 1947-1950;
8. a) Adjé, N.; Brouilles, P.; Uguen, D. Tetrahedron Lett. 1993, 34, 4631-4634, note 4; Takasu, M.; Naruse, Y.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 1947-1950;
9. b) Ricci, A.; Roelens, S.; Vannucchi, A. J. Chem. Soc. Chem. Commun. 1985, 1457-1458; Bredenkamp, M. W.; Flowers, H. M.; Holzapfel, C. W. Chem. Ber. 1992, 125, 1159-1167;
10. b) Ricci, A.; Roelens, S.; Vannucchi, A. J. Chem. Soc. Chem. Commun. 1985, 1457-1458; Bredenkamp, M. W.; Flowers, H. M.; Holzapfel, C. W. Chem. Ber. 1992, 125, 1159-1167;
11. c) Rebière, F.; Kagan, H. B. Tetrahedron Lett. 1989, 30, 3659-3662; Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538-7339; Lohray, B. B. Synthesis 1992, 1035-1052, and references therein.
12. c) Rebière, F.; Kagan, H. B. Tetrahedron Lett. 1989, 30, 3659-3662; Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538-7339; Lohray, B. B. Synthesis 1992, 1035-1052, and references therein.
13. c) Rebière, F.; Kagan, H. B. Tetrahedron Lett. 1989, 30, 3659-3662; Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538-7339; Lohray, B. B. Synthesis 1992, 1035-1052, and references therein.
14. For n=4, THF can be used (Mosset, P.; Grée, R.; Falck, J. R. Synth. Commun. 1989, 19, 645-658; Gruiec, R.; Noiret, N.; Patin, H. Bull. Soc. Chim. Fr. 1994, 131, 699-705. See also ref. 9a).
15. For n=4, THF can be used (Mosset, P.; Grée, R.; Falck, J. R. Synth. Commun. 1989, 19, 645-658; Gruiec, R.; Noiret, N.; Patin, H. Bull. Soc. Chim. Fr. 1994, 131, 699-705. See also ref. 9a).
16. Breuilles, P.; Schmittberger, T.; Uguen, D. Tetrahedron Lett. 1993, 34, 4205-4208.
17. Lipase from Candida cylindracea, another cheap enzyme, gave less satisfactory results.
18. 2/ether) to afford the pure monoester. With n=8, a substantial amount of diol was also formed; possibly the extended lipophilicity of the chain outweighs any change resulting from substitution of an acetoxy residue by the hydroxy group and tends to reduce the difference in binding of both the bis-and the mono-acetate to the enzyme.
19. a) Aksnes, G. Acta Chem. Scand. 1961, 15, 438-440;
20. b) Yamamoto, S.-I.; Okuma, K.; Ohta, H. Bull. Chem. Soc. Jpn 1988, 61, 4476-4478;
21. b) Buss, A. D.; Greeves, N.; Levin, D.; Wallace, P.; Warren, S. Tetrahedron Lett. 1984, 25, 357-360. The phosphine oxide 6b has also be obtained from butyrolactone (Wallace, P.; Warren, S. J. Chem. Soc. Perkin I 1988, 2971-2978).
22. b) Buss, A. D.; Greeves, N.; Levin, D.; Wallace, P.; Warren, S. Tetrahedron Lett. 1984, 25, 357-360. The phosphine oxide 6b has also be obtained from butyrolactone (Wallace, P.; Warren, S. J. Chem. Soc. Perkin I 1988, 2971-2978).
23. a) Pattison, F. L. M.; Stothers, J. B.; Woolford, R. G. J. Am. Chem. Soc. 1956, 78, 2255-2259;
24. b) Kang S.-K.; Kim, W.-S.; Moon, B.-H. Synthesis, 1985, 1161-1162, and references therein.
25. Ireland, R.; Walba, D. M. Organic Syntheses 1977, 56, 44-48. Treatment of the bromohydrins 8b,c by triphenylphosphine, followed by hydrolysis of the resulting phosphonium bromides with alkali (ref. 9a) proved less satisfactory, the yield in phosphonium salts being only moderate. For prior conversion of the bromohydrins into the corresponding bromoacetates, see: Bestmann, H. J.; Koschatzky, K. H.; Schätzke, W., Süß, J.; Vostrowsky, O. Liebigs Ann. Chem. 1981, 1705-1720.
26. Ireland, R.; Walba, D. M. Organic Syntheses 1977, 56, 44-48. Treatment of the bromohydrins 8b,c by triphenylphosphine, followed by hydrolysis of the resulting phosphonium bromides with alkali (ref. 9a) proved less satisfactory, the yield in phosphonium salts being only moderate. For prior conversion of the bromohydrins into the corresponding bromoacetates, see: Bestmann, H. J.; Koschatzky, K. H.; Schätzke, W., Süß, J.; Vostrowsky, O. Liebigs Ann. Chem. 1981, 1705-1720.
27. 3) data: 3a: 1.6-1.8 (m, 2H), 2.07 (s, 3H), 2.08-2.22 (m, OH), 3.71 (t, J=6Hz, 2H), 4.24 (t, J=6.1Hz, 2H); 3b: 1.61-1.77 (m, 4H+ OH), 2.06 (s, 3H), 3.69 (t, J=6.1Hz, 2H), 4.11 (t, J=6.3Hz, 2H); 3c: 1.38-1.50 (m, 2H+ OH), 1.53-1.74 (m, 4H), 2.05 (s, 3H), 3.65 (t, J=6.2Hz, 2H), 4.07 (t, J=6.5Hz, 2H); 3d: 1.35-1.56 (m, 4H+ OH), 1.58-1.7 (m, 4H), 2.05 (s, 3H), 3.64 (t, J=6.4Hz, 2H), 4.06 (t, J=6.6Hz, 2H); 3e: 1.3-1.4 (m, 8H+ OH), 1.53-1.72 (m, 4H), 2.04 (s, 3H), 3.63 (t, J=6.4Hz, 2H), 4.04 (t, J=6.6Hz, 2H); 5: 1.81-2.04 (m, OH), 2.11 (s, 3H), 4.33 (t, J=1.8Hz, 2H), 4.72 (t, J=1.8Hz, 2H); 6b: 1.63-1.49 (m, 4H), 2.23-2.37 (m, 2H), 2.86-2.91 (m, OH), 3.58-3.66 (m, 2H), 7.39-7.54 (m, 6H), 7.66-7.77 (m, 4H); 6c: 1.46-1.67 (m, 6H), 1.76 (m, OH), 2.16-2.34 (m, 2H), 3.55-3.63 (m, 2H+ OH), 7.40-7.56 (m, 6H), 7.61-7.75 (m, 4H); 9b: 1.49-1.57 (m, 2H), 1.63-1.73 (m, 2H), 2.03-2.11 (m, 2H), 3.63 (t, J=6.42Hz, 2H), 7.3-7.46 (m, 1OH); 9c: 1.47-1.55 (m, 6H), 2.02-2.09 (m, 2H), 3.6 (t, J=6.12Hz, 2H), 7.29-7.46 (m, 10H).
28. Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911-937.