Synthesis of enantiomerically pure (R)-and (S)-1-benzoyloxypropane-2,3-diol and revision of the stereochemical outcome of the Candida antarctica lipase-catalyzed benzoylation of glycerol

Tetrahedron Asymmetry

Volumn 22, Issue 6, 2011, Pages 658-661

  Casati, Silvana ^a   Ciuffreda, Pierangela ^a   Santaniello, Enzo ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 BENZOYLOXYPROPANE 2,3 DIOL; GLYCEROL; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA ANTARCTICA; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 79956341065     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2011.04.003     Document Type: Article

References (24)

1. J. Padmakumari Amma, and J.K. Stille J. Org. Chem. 47 1982 468 473
2. F. Leurquin, T. Ozturk, M. Pilkington, and J.D. Wallis J. Chem. Soc., Perkin Trans. 1 1997 3173 3177
3. K. Nacro, D.M. Sigano, S. Yan, M.C. Nicklaus, L.L. Pearce, N.E. Lewin, S.H. Garfield, P.M. Blumberg, and V.E. Marquez J. Med. Chem. 44 2001 1892 1904
4. F. Aragozzini, E. Maconi, D. Potenza, and C. Scolastico Synthesis 1989 225 227
5. J. Balint, G. Egri, A. Kolbert, C. Dianoczky, E. Fogassy, L. Novak, and L. Poppe Tetrahedron: Asymmetry 10 1999 4017 4028
6. T. Tsujigami, T. Sugai, and H. Ohta Tetrahedron: Asymmetry 12 2001 2543 2549
7. Y. Kato, I. Fujiwara, and Y. Asano Bioorg. Med. Chem. Lett. 9 1999 3207 3210
8. Y. Kato, I. Fujiwara, and Y. Asano J. Mol. Catal. B: Enzym. 9 2000 193 200
9. J.-H. Xu, Y. Kato, and Y. Asano Biotechnol. Bioeng. 73 2001 493 499
10. E. Baer, I.B. Cushing, and H.O.L. Fischer Can. J. Res., B 21 1943 119 124
11. J. LeCocq, and C.E. Ballou Biochemistry 3 1964 976 980
12. E. Caytan, Y. Cherghaoui, C. Barril, C. Jouitteau, C. Rabiller, and G.S. Remaud Tetrahedron: Asymmetry 17 2006 1622 1624
13. For a review see: J. Jurczak, S. Pikul, and T. Bauer Tetrahedron 42 1986 447 488
14. 13C NMR analysis
15. C.C. Yu, Y.-S. Lee, B.S. Cheon, and S.H. Lee Bull. Korean Chem. Soc. 24 2003 1229 1231
16. E. Santaniello, P. Ciuffreda, S. Casati, L. Alessandrini, and A. Repetto J. Mol. Catal. B: Enzym. 40 2006 81 85
17. J.A. Dale, D.L. Dull, and H.S. Mosher J. Org. Chem. 34 1969 2543 2549
18. K.W.C. Poon, K.M. Lovell, K.N. Dresner, and A. Datta J. Org. Chem. 73 2008 752 755
19. J.-D. Lee, M. Ueno, Y. Miyajima, and H. Nakamura Org. Lett. 9 2007 323 326
20. R. Katoch, G.K. Trivedi, and R.S. Phadke Bioorg. Med. Chem. 7 1999 2753 2758
21. Kato et al. (Refs. 5-7 ) assigned an (R)-configuration to (+)-1c referring to the negative specific rotation recorded for (-)-3-O-benzyl-sn- glycerol by M. Yodo, Y. Matsushita, E. Ohsugi, and H. Harada Chem. Pharm. Bull. 36 1988 902 913 erroneously referring to this compound as to (S)-1c
22. Compound (R)-1c has been prepared by another enzymatic approach; see: D. Breitgoff, K. Laumen, and M.P. Schneider J. Chem. Soc., Chem. Commun. 1986 1523 1524 This biocatalytic protocol starts with the asymmetrization of the 1,3-diacetate of 2-benzyloxyglycerol via lipase-catalyzed hydrolysis. This allowed the preparation of the corresponding monoacetate (53% conversion, 75% yield of purified product) which was transformed into (R)-(-)-1c in three additional steps (yields not reported)
23. R.T. Sawant, and S.B. Waghmode Tetrahedron 66 2010 2010 2014
24. C.R. Noe, M. Knollmüller, C. Miculka, K. Dungler, E. Wagner, and P. Ettmayer Chem. Ber. 127 1994 887 892