Highly diastereoselective synthesis of anomeric β-O-glycopyranosyl carbamates from isocyanates

Synthesis

Volumn , Issue 11, 1996, Pages 1309-1312

  Leenders, Ruben G G ^a   Ruytenbeek, Rob ^a   Damen, Eric W P ^a   Scheeren, Hans W ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

1 O glycopyranosyl carbamates; Curtius rearrangement; isocyanates; prodrug preparation; diastereoselectivity

Indexed keywords

CARBAMIC ACID DERIVATIVE; CARBOHYDRATE DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029821617     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4377     Document Type: Article

References (29)

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2. (b) Leenders, R. G. G.; Damen, E. W. P.; Scheeren, J. W.; Haisma, H. J.; Houba, P. H. J.; de Vos, D. European Patent 1995, 95 201 747.
3. (c) Leenders, R. G. G.; Scheeren, J. W.; Houba, P. H. J.; Boven, E.; Haisma, H. J. Bioorg. Med. Chem. Lett. 1995, 5, 2975.
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5. ADEPT: Antibody Directed Enzyme Prodrug Therapy. For recent reviews, see: (a) Senter, P. D.; Wallace, P. M.; Svensson, H. P.; Vrudhula, V. M.; Kerr, D. E.; Hellström, I.; Hellström, K. E. Bioconjugate Chem. 1993, 4, 3. (b) Jungheim, L. N.; Shephard, T. A. Chem. Rev. 1994, 94, 1553. (c) Bagshawe, K. D. J. Contr. Rel. 1994, 28, 187. (d) Niculescu-Duvaz, I.; Springer, C. J. Current Med. Chem. 1995, 2, 687.
6. ADEPT: Antibody Directed Enzyme Prodrug Therapy. For recent reviews, see: (a) Senter, P. D.; Wallace, P. M.; Svensson, H. P.; Vrudhula, V. M.; Kerr, D. E.; Hellström, I.; Hellström, K. E. Bioconjugate Chem. 1993, 4, 3. (b) Jungheim, L. N.; Shephard, T. A. Chem. Rev. 1994, 94, 1553. (c) Bagshawe, K. D. J. Contr. Rel. 1994, 28, 187. (d) Niculescu-Duvaz, I.; Springer, C. J. Current Med. Chem. 1995, 2, 687.
7. ADEPT: Antibody Directed Enzyme Prodrug Therapy. For recent reviews, see: (a) Senter, P. D.; Wallace, P. M.; Svensson, H. P.; Vrudhula, V. M.; Kerr, D. E.; Hellström, I.; Hellström, K. E. Bioconjugate Chem. 1993, 4, 3. (b) Jungheim, L. N.; Shephard, T. A. Chem. Rev. 1994, 94, 1553. (c) Bagshawe, K. D. J. Contr. Rel. 1994, 28, 187. (d) Niculescu-Duvaz, I.; Springer, C. J. Current Med. Chem. 1995, 2, 687.
8. ADEPT: Antibody Directed Enzyme Prodrug Therapy. For recent reviews, see: (a) Senter, P. D.; Wallace, P. M.; Svensson, H. P.; Vrudhula, V. M.; Kerr, D. E.; Hellström, I.; Hellström, K. E. Bioconjugate Chem. 1993, 4, 3. (b) Jungheim, L. N.; Shephard, T. A. Chem. Rev. 1994, 94, 1553. (c) Bagshawe, K. D. J. Contr. Rel. 1994, 28, 187. (d) Niculescu-Duvaz, I.; Springer, C. J. Current Med. Chem. 1995, 2, 687.
9. In collaboration with the group of Dr. E. Boven and Dr. H. J. Haisma, Department of medical oncology, Free University of Amsterdam, the Netherlands.
10. Previously we found that β-glucuronyl carbamates are hydrolyzed by β-glucuronidase efficiently: N-phenyl 1-β-O-glucuroyl carbamate and 4-nitrophenyl β-glucuronide are hydrolyzed by β-glucuronidase at a comparable rate.
11. See, for example: (a) Dow, J.; Piriou, F.; Wolf, E.; Dulery, B. D.; Haegele, K. D. Drug Metabol. Disp. 1994, 22, 738. (b) Brown, S. Y.; Garland, W. A.; Fukada, E. K. Drug Metabol. Disp. 1990, 18, 546.
12. See, for example: (a) Dow, J.; Piriou, F.; Wolf, E.; Dulery, B. D.; Haegele, K. D. Drug Metabol. Disp. 1994, 22, 738. (b) Brown, S. Y.; Garland, W. A.; Fukada, E. K. Drug Metabol. Disp. 1990, 18, 546.
13. See, for example: (a) Tremaine, L. M.; Stroh, J. G.; Ronfeld, R. A. Drug Metabol. Disp. 1989, 17, 58. (b) Straub, K.; Davis, M.; Hwang, B. Drug Metabol. Disp. 1988, 16, 359.
14. See, for example: (a) Tremaine, L. M.; Stroh, J. G.; Ronfeld, R. A. Drug Metabol. Disp. 1989, 17, 58. (b) Straub, K.; Davis, M.; Hwang, B. Drug Metabol. Disp. 1988, 16, 359.
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21. The anomeric composition of 1a in different solvents was determined using the respective signals of H-5(α) and H-5(β) which were obtained on a 100 MHz FT-NMR spectrometer. The H-1(α) and H-1(β) signals could not be used because of overlap with other signals.
22. Schmidt, R. R. Angew. Chem. 1986, 98, 213; Angew. Chem., Int. Ed. Engl. 1986, 25, 212.
23. Schmidt, R. R. Angew. Chem. 1986, 98, 213; Angew. Chem., Int. Ed. Engl. 1986, 25, 212.
24. Less than a stoichiometric amount of 1 is added because a fraction of the in situ formed isocyanate dimerizes. In case of 21, 22 % of the symmetrical urea was isolated after completion of the reaction.
25. Braun, H.; Wiessler, M. Angew. Chem. 1980, 92, 407; Angew. Chem., Int. Ed. Engl. 1980, 19, 400.
26. Braun, H.; Wiessler, M. Angew. Chem. 1980, 92, 407; Angew. Chem., Int. Ed. Engl. 1980, 19, 400.
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29. In the 400 MHz proton spectrum, all signals are double due to restricted rotation around the Ar-Ar bond. The double signals coalesce on heating. In the 100 MHz proton spectrum, only the NH signal is double.