Practical One-Pot Synthesis of Protected l-Glyceraldehyde Derivatives

Abstract

A large-scale, simple, economic, and safe procedure for the preparation of l-glyceraldehyde acetonide under conditions, which allow its direct transformation (one-pot) into the desired products (acetylene, imine, nitrone, unsaturated ester) is reported. l-Glyceraldehyde acetonide is obtained from the corresponding ester, which is readily available from l-serine.

Key words

l-glyceraldehyde acetonide - l-glyceraldehyde derivatives - aldehydes - nitrones - acetylenes

• References

• 1 Paquett LA. Handbook of Reagents for Organic Synthesis: Chiral Reagents for Asymmetric Synthesis. Wiley; New York: 2003: 255
• 2 Mulzer J In Organic Synthesis Highlights. Altenback H.-J. VCH Verlag; Weinheim: 1991: 243
• 3 Jurczak J, Pikul S, Bauer T. Tetrahedron 1986; 42: 447
• 4 Jung ME, Shaw TJ. J. Am. Chem. Soc. 1980; 102: 6304
• 5 Kesteleyn BR. R, Surleraux DL. N. G. PCT Int. Appl WO 2003/022853, 2003 ; Chem. Abstr. 2003, 138, 238003
• 6 Tung RD, Salituro FG, Deininger DD, Murcko MA, Novak PM, Bhisetti GR. PCT Int. Appl WO 1995/24385, 1995 ; Chem. Abstr. 1995, 124, 116874
• 7 Sherrill RG, Hale MR, Spaltenstein A, Furfine ES, Andrews CW, Lowen GT. PCT Int. Appl WO 1999/65870, 1999 ; Chem. Abstr. 1999, 132, 49801
• 8 Hale MR, Baker CT, Stammers TA, Sherrill RG, Spaltenstein A, Furfine ES, Maltais F, Andrews CW, Miller JF, Samano V. PCT Int. Appl WO 2000/47551, 2000 ; Chem. Abstr. 2000, 133, 177157
• 9 Hale MR, Tung R, Price S, Wilkes RD, Schairer WC, Jarvis AN, Spaltenstein A, Furfine ES, Samano V, Kaldor I, Miller JF, Brieger MS. PCT Int. Appl WO 2000/76961, 2000 ; Chem. Abstr. 2000, 134, 56676
• 10 Vazquez ML, Mueller RA, Talley JJ, Getman DP, Decrescenzo GA, Freskos JN, Heintz RM, Bertenshaw DE. EP 0715618, 2000 ; Chem. Abstr. 2000, 132, 322147
• 11 Wigerinck PT. B. P, Wang G, Eissenstat M, Erickson JW. PCT Int. Appl WO 2001/25240, 2001 ; Chem. Abstr. 2001, 134, 295811
• 12 Erickson JW, Gulnik SV. PCT Int. Appl WO 1999/67417, 1999 ; Chem. Abstr. 1999, 132, 59135
• 13a Schmid CR, Bryant JD, Dowlatzedah M, Phillips JL, Prather DE, Schnatz RD, Sear NL, Vianco CS. J. Org. Chem. 1991; 56: 4056
• 13b Schmid CR, Bryant JD. Org. Synth. 1995; 72: 6
• 14 Andrews GC, Crawford TC, Bacon BE. J. Org. Chem. 1981; 46: 2976
• 15a Hubschwerlin C. Synthesis 1986; 962
• 15b Hubschwerlin C, Specklin J.-L, Higelin J. Org. Synth. 1995; 72: 1
• 16 Danielmeier K, Steckhan E. Tetrahedron: Asymmetry 1995; 6: 1181
• 17 Abushanab E, Vemishetti P, Leiby RW, Singh HK, Mikkilineni AB, Wu DC.-J, Saibaba R, Panzica RP. J. Org. Chem. 1988; 53: 2598
• 18 Mizuno Y, Sugimoto K. US Patent 4567282, 1986 ; Chem. Abstr. 1985, 103, 178573
• 19 Quaedflieg P, Lommen F, Vijn BJ, Van Boxtel D. PCT Int. Appl WO 2005/037819A1, 2005 ; Chem. Abstr. 2005, 142, 430488
• 20 Mukaiyama T, Shiina I, Iwadare H, Saitoh M, Nishimura T, Ohkawa N, Sakoh H, Nishimura K, Tani Y.-i, Hasegawa M, Yamada K, Saitoh K. Chem.–Eur. J. 1999; 5: 121
• 21 Czeskis B. J. Labelled Comp. Radiopharm. 1998; 41: 465
• 22 Hirth G, Walther W. Helv. Chim. Acta 1985; 68: 1863
• 23 Michalak M, Stodulski M, Stecko S, Mames A, Soluch M, Panfil I, Furman B, Chmielewski M. J. Org. Chem. 2011; 76: 6931
• 24 Ohira S. Synth. Commun. 1989; 19: 561
• 25 Muller S, Roth LB, Bestmann HJ. Synlett 1996; 521
• 26 Merino P, Franco S, Merchan FL, Tejero T. Tetrahedron: Asymmetry 1997; 8: 3489
• 27 Merino P In Science of Synthesis. Vol. 27. Padwa A. Thieme; Stuttgart: 2004: 511
• 28 Huang J.-P, Zhao L, Gu S.-X, Wang Z.-H, Zhang H, Chen F.-E, Dai H.-F. Synthesis 2011; 555
• 29 Quaedflieg PJ. L. M, Kesteleyn BR. R, Wigerinck PB. T. P, Goyvaerts NM. F, Vijn RJ, Liebregts CS. M, Kooistra JH. M. H, Cusan C. Org. Lett. 2005; 7: 5917
• 30 Pietruszka J, Witt A. J. Chem. Soc., Perkin Trans. 1 2000; 4293