Synthesis of 6-Deoxy-4-aminohexoses from Cyclopentanones

Abstract

Procedures for the conversion of (±)-2-methoxy-2-methyl-3-oxazolidinylcyclopentanone into a variety of 4-amino-6-de-oxyhexoses have been developed. These involve Baeyer-Villiger ring expansions, reductive methylations and epimerizations.

Keywords

(±)-2-methoxy-2-methyl-3-oxazolidinylcyclopentan-one - 4-amino-6-deoxyhexoses - Baeyer-Villiger ring expansions - reductive methylation - epimerizations

References

• 1 Pelyvas I. Monneret C. Herczegh P. Synthetic Aspects of Aminodeoxy Sugars and Antibiotics   Springer-Verlag; New York: 1988. 
• 2a Stevens CL. Gutowski GE. Bryant CP. Glinski RP. Tetrahedron Lett.  1969,  1181 
• 2b Malik A. Afza N. Voelter W. J. Chem. Soc., Perkin Trans. 1  1983,  2103 
• 2c

  See also reference 27.

• 3a Leet JE. Schroeder DR. Hofstead SJ. Golik J. Colson KL. Huang S. Klohr SE. Doyle TE. Matson JA. J. Am. Chem. Soc.  1992,  114:  7946 
• 3b Hornyak M. Pelyvas IF. Sztaricskai FJ. Tetrahedron Lett.  1993,  34:  4087 
• 3c Vuljanic T. Kihlberg J. Somfai P. Tetrahedron Lett.  1994,  35:  6937 
• 3d Vuljanic T. Kihlberg J. Somfai P. J. Org. Chem.  1988,  63:  279 
• 3e Lear MJ. Hirama M. Tetrahedron Lett.  1999,  4897 
• 4 Smith GR. Finley JJIV. Guiliano RM. Carbohydr. Res.  1988,  308:  223 
• 5 Iida K. Ishii T. Hirama M. Otani T. Minami Y. Yoshida K. Tetrahedron Lett.  1993,  34:  4079 
• 6a Koskinen AMP. Otsomaa LA. Tetrahedron  1997,  53:  6473 
• 6b

  See references 22-24 within reference 27a.

• 7 Yoshimura J. Aqeel A. Sato K. Singh RB. Hashimoto H. Carbohydr. Res.  1987,  166:  253 
• 8 Fronza G. Fuganti C. Grasselli P. Pedrocchi-Fantoni G. Carbohydr. Res.  1985,  136:  115 
• 9 Hegedus LS. Bates RW. Soderberg BC. J. Am. Chem. Soc.  1991,  113:  923 
• 10a Miller M. Hegedus LS. J. Org. Chem.  1993,  58:  6779 
• 10b Reed AD. Hegedus LS. J. Org. Chem.  1995,  60:  3787 
• 10c Kedar TE. Miller MW. Hegedus LS. J. Org. Chem.  1996,  61:  6121 
• 11 Reed AD. Hegedus LS. Organometallics  1997,  16:  2313 
• 12a Brown B. Hegedus LS. J. Org. Chem.  1998,  63:  8012 
• 12b Brown B. Hegedus LS. J. Org. Chem.  2000,  65:  1805 
• 12c Hegedus LS. Geisler L. J. Org. Chem.  2000,  65:  4200 
• 13 Wen X. Norling H. Hegedus LS. J. Org. Chem.  2000,  65:  2096 
• 14a Encyclopedia of Reagents for Organic Synthesis   Paquette LA. Wiley; Chichester: 1995.  p.1516 ; and references therein
• 14b Reeder LM. Hegedus LS. J. Org. Chem.  1999,  64:  3306 
• 15 Dahanukar VH. Rychnovsky SD. J. Org. Chem.  1996,  61:  8317 
• 16 Carpino LA. Tunga A. J. Org. Chem.  1986,  51:  1930 
• 18 Borch RF. Bernstein MD. Durst HD. J. Am. Chem. Soc.  1971,  93:  2897 
• 19 Abdel-Magid AF. Carson KG. Harris BD. Maryanoff CA. Shah RD. J. Org. Chem.  1996,  61:  3849 
• 20a Davis FA. Stringer OD. Billmers JM. Tetrahedron Lett.  1983,  24:  1213 
• 20b Davis FA. Sheppard AC. Tetrahedron  1989,  45:  5703 
• 20c Davis’ reagent was prepared according to the literature, see: Davis FA. Lamendola J. Nadir U. Kluger EW. Sedergran TC. Panunto TW. Billmers R. Jenkins R. Turchi IJ. Watson WH. Chen JS. Kimura M. J. Am. Chem. Soc.  1980,  102:  2000 
• 20d See also: Davis FA. Chattopadhyay S. Towson JC. Lal S. Reddy T. J. Org. Chem.  1988,  53:  2087 
• 21a Meyers AI. Tschantz MA. Brengel GP. J. Org. Chem.  1995,  60:  4359 
• 21b Reich HJ. Wollowitz S. Trend JE. Chow F. Wendleborn DF. J. Org. Chem.  1978,  43:  1697 
• 22 Van Der Deen H. VanOeveren A. Kellog RM. Feringa BL. Tetrahedron Lett.  1999,  40:  1755 
• 23a Cha JK. Christ WJ. Kishi Y. Tetrahedron  1984,  40:  2247 
• 23b

  Also see ref. 5 and 27.

• 24 Kutney JP. Ratcliffe AH. Synth. Commun.  1975,  5:  47 
• 25a Molander GA. Org. React.  1994,  46:  211 
• 25b Brown B. Hegedus LS. J. Org. Chem.  1998,  63:  8012 
• 26a Shing TK. Tai VW.-F. Tam EK. Angew. Chem., Int. Ed. Engl.  1994,  33:  2312 
• 26b Reed AD. Hegedus LS. J. Org. Chem.  1995,  60:  3787 
• 27a Marmor S. J. Org. Chem.  1963,  28:  250 
• 27b Honda T. Takada H. Miki S. Tsubuki M. Tetrahedron Lett.  1993,  34:  8275 
• 28 Renoud-Grapping M. Vanucci C. Lhommet G. J. Org. Chem.  1994,  59:  3902 
• 29 Adam W. Hadjiarapoglou L. Nestler B. Tetrahedron Lett.  1990,  31:  331 
• 30 Reeder LM. Hegedus LS. J. Org. Chem.  1999,  64:  3306 

17

Other investigators have also reported low methylation yields and cited high volatility as a factor. See ref. 3b and 3e.