Practical and efficient synthesis of a chiral C5 building block, 2-O-allyl-D-arabinose, from diacetone-D-glucose

Synthesis

Volumn , Issue 9, 2006, Pages 1461-1464

  Storz, Thomas ^a,b   Vasella, Andrea ^a  

^a ETH ZURICH   (Switzerland)

^b AMGEN INC   (United States)

Author keywords

Allyl; Carbohydrates; D arabinose; Hemiacetals; Oxidation; Periodate cleavage

Indexed keywords

ALLYL RESINS; CARBOHYDRATES; ETHERS; GLUCOSE; OXIDATION; SYNTHESIS (CHEMICAL);

D-ARABINOSE; DIACETONE GLUCOSE; HEMIACETALS; PERIODATE CLEAVAGE;

ORGANIC COMPOUNDS;

2 O ALLYL DEXTRO ARABINOSE; 2 O ALLYLPENTOSE; ARABINOSE; GLUCOSE DERIVATIVE; PENTOSE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; SYNTHESIS;

EID: 33646588357     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926418     Document Type: Article

References (25)

1. (a) As of December 2005, to the best of our knowledge, the only published reference to a 2-O-allylpentose consists of a patent (Isis Corp.): Cook, P. D. WO 9313121,1993.
2. (b) For 2-O-allyl-D-ribose no preparation was described.
3. (a) 3-O-Allyl-D-glucose: Hoiness, D. E.; Wade, C. P.; Rowland, S. P. Can. J. Chem. 1968, 46, 667.
4. (b) Ito, H.; Eby, R.; Kramer, S.; Schuerch, C. Carbohydr. Res. 1980, 86, 193.
5. (c) Takeo, K.; Nakaji, T.; Shinmitsu, K. Carbohydr. Res. 1984, 133, 275.
6. (d) Liu, C. M.; Warren, C. D.; Jeanloz, R. W. Carbohydr. Res. 1985, 136, 273.
7. (e) Bhattacharjya, A.; Chattopadhyay, P.; McPhail, A. T.; McPhail, D. R. J. Chem. Soc., Chem. Commun. 1990, 1508.
8. (a) 3-O-Allyl-D-allose and 3-O-allyl-D-altrose: Shing, T. K. M.; Zhong, Y.-L.; Mak, T. C. W.; Wang, R.-J.; Xue, F. J. Org. Chem. 1998, 63, 414.
9. (b) Shing, T. K. M.; Zhong, Y.-L. Tetrahedron 2001, 57, 1573.
10. 3-O-Allyl-D-galactose: Srivastava, G.; Hindsgaul, O. J. Carbohydr. Chem. 1991, 10, 927.
11. 3-O-Allyl-D-mannose: Masanao, M.; Ogawa, T. JP 56036497, 1981.
12. For cytotoxic and antimicrobial activity of 3-O-alkyl-D-glucoses, 3-O-alkenyl-D-glucoses, and 3-O-alkenyl-D-alloses, see: Ikekawa, T.; Irinoda, K.; Saze, K.; Katori, T.; Matsuda, H.; Ohkawa, M.; Kosik, M. Chem. Pharm. Bull. 1987, 35, 2894.
13. 16
14. (a) There is evidence that D-glucose and D-galactose are oxidized by sodium periodate predominantly in the pyranose form: Hough, L.; Taylor, T. J.; Thomas, G. H. S.; Woods, B. M. J. Chem. Soc. 1958, 1212.
15. (b) There is very little published about the behavior of 3-O-alkylhexoses and 3-O-alkenylhexoses under these conditions. Barker and Smith claimed that the oxidation of 3-O-methylglucose with sodium periodate led to 4-O-formyl-2-O-methylarabinose, but without structural proof: Barker, G. R.; Smith, D. C. C. Chem. Ind. 1952, 1035.
16. (c) On the other hand, Qadir and Webber had reported on the instability of an allyl ether protective group in a sodium periodate-mediated oxidation of a cyclic sulfide: Qadir, M. H.; Webber, J. M. J. Chem. Soc. Pak. 1986, 8, 19.
17. 4, glacial AcOH] of the Perlin-Brice synthesis of D-erythrose from D-glucose the initial reaction product has been reported as 3,4-di-O-formyl-D-erythrose: (a) Perlin, A. S.; Brice, C. Can. J. Chem. 1956, 34, 541.
18. (b) Perlin, A. S. Meth. Carbohydr. Chem. 1962, 1, 64.
19. (c) To the best of our knowledge, there are no literature reports on the hydrolytic stability of formate esters in allyl ether protected hexoses or pentoses.
20. 3c).
21. SciFinder/Beilstein searches, 12/2005. Strangely, upon contact of 1 with the skin of the fingers, an apparent muscular tickling/twitching effect lasts several minutes (anecdotal observation by T. S.).
22. Storz, T.; Vasella, A. Helv. Chim. Acta 1998, 81, 1896.
23. Takeo, K.; Nakagen, M.; Teramoto, Y. Carbhohydr. Res. 1990, 201, 261.
24. Smith, A. B. III; Rivero, R. A.; Hale, K. J.; Vacaro, H. A. J. Am. Chem. Soc. 1991, 113, 2092.
25. Bols, M. In Carbohydrate Building Blocks, 1st ed.; Wiley & Sons: New York, 1996, 11.