Synthesis of Enantiomers of Butane-1,2-diacetal-Protected Glyceraldehyde and of (R,R)-Butane-1,2-diacetal-Protected Glycolic Acid

Patrick Michel; Steven V. Ley

doi:10.1055/s-2003-40519

PAPER

Synthesis of Enantiomers of Butane-1,2-diacetal-Protected Glyceraldehyde and of (R,R)-Butane-1,2-diacetal-Protected Glycolic Acid

Patrick Michel, Steven V. Ley*
Department of Chemistry, University of Cambridge
Fax: Lensfield Road, Cambridge, CB2 1EW, UK; e-Mail: svl1000@cam.ac.uk;

Abstract

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Abstract

A convenient and scalable synthesis of enantiomers of butane-2,3-diacetal-protected glyceraldehyde was accomplished from d-mannitol and l-ascorbic acid, respectively. The R-aldehyde was additionally converted to the (R,R)-butane-2,3-diacetal glycolic acid building block 1.

Key words

diacetal - glyceraldehydes - α-hydroxy acid - d-mannitol - l-ascorbic acid

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Referenzen

References

1a Coppola GM. Schuster HF. α-Hydroxy Acids in Entantioselective Synthesis VCH; Weinheim: 1997.

1b Hanessian S. Total Synthesis of Natural Products: The Chiron Approach Pergamon; Oxford: 1983.

2a Helmchen G. Wierzchowski R. Angew. Chem., Int. Ed. Engl 1984, 23: 60

2b Kelly TR. Arvanitis A. Tetrahedron Lett. 1984, 25: 39

2c Enomoto M. Ito Y. Katsuki T. Yamaguchi M. Tetrahedron Lett. 1985, 26: 1343

2d Cardillo G. Orena M. Romero M. Sandri S. Tetrahedron 1989, 45: 1501

2e Crimmins MT. Emmitte KA. Katz JD. Org. Lett. 2000, 2: 2165

2f Jung JE. Ho H. Kim H.-D. Tetrahedron Lett. 2000, 41: 1793

2g Yu H. Ballard CE. Wang D. Tetrahedron Lett. 2001, 42: 1835

3a Ludwig JW. Newcomb M. Bergbreiter DE. Tetrahedron Lett. 1986, 27: 2731

3b Renaud P. Seebach D. Angew. Chem., Int. Ed. Engl. 1986, 25: 843

3c Pearson WH. Cheng M.-C. J. Org. Chem. 1986, 51: 3746

3d Pearson WH. Cheng M.-C. J. Org. Chem. 1987, 52: 3176

3e Renaud P. Abazi S. Helv. Chim. Acta 1996, 79: 1696

3f Chang J.-W. Jang D.-P. Uang B.-J. Liao F.-L. Wang S.-L. Org. Lett. 1999, 1: 2061

3g Andrus MB. Soma Sekhar BBV. Meredith E. Dalley NK. Org. Lett. 2000, 2: 3035

4a Ley SV. Downham R. Edwards PJ. Innes JE. Woods M. Contemp. Org. Synth. 1995, 2: 365

4b Downham R. Kim KS. Ley SV. Woods M. Tetrahedron Lett. 1994, 35: 769

4c Boons G.-J. Downham R. Kim KS. Ley SV. Woods M. Tetrahedron 1994, 50: 7157

4d Fujita M. Lainé D. Ley SV. J. Chem., Perkin Trans. 1 1999, 1647

5a Berens U. Leckel D. Oepen SC. J. Org. Chem. 1995, 60: 8204

5b Ley SV. Baeschlin DK. Dixon DJ. Foster AC. Ince SJ. Priepke HWM. Reynolds DJ. Chem. Rev. 2001, 101: 53

6a Diez E. Dixon DJ. Ley SV. Angew. Chem. Int. Ed. 2001, 40: 2906

6b Dixon DJ. Ley SV. Polara A. Sheppard T. Org. Lett. 2001, 3: 3749

6c Dixon DJ. Guarna A. Ley SV. Polara A. Rodriguez F. Synthesis 2002, 1973

6d Dixon DJ. Ley SV. Rodriguez F. Org. Lett. 2001, 3: 3753

6e Dixon DJ. Ley SV. Rodriguez F. Angew. Chem. Int. Ed. 2001, 40: 4763

7 Michel P. Ley SV. Angew. Chem. Int. Ed. 2002, 41: 3898

8 Lichtenthaler FW. Jarglis P. Lorenz K. Synthesis 1988, 790

9a Isbell HS. Frush HL. Carbohydr. Res. 1979, 72: 301

9b Wei CC. De Bernardo S. Tengi JP. Borgese J. Weigele M. J. Org. Chem. 1985, 50: 3462

9c Abushanab E. Vemishetti P. Leiby RW. Singh HK. Mikkilineni AB. Wu DC.-J. Saibaba R. Panzica RP. J. Org. Chem. 1988, 53: 2598

10

[α]_D of this aldehyde in CHCl₃ is not reliable because the value increases from -110 to -160 in two hours possibly due to an acid-catalysed decomposition. Nevertheless, the enantiomeric excess of 1 determined by chiral GC proved that the enantiomeric excess of 6 is at least 99%.