Synthesis of 6-amino-3,5-deoxyinositol 1-phosphates via (1R,2R,4R,6S)- 1,6-epoxy-2,4-bis-benzyloxycyclohexane aminolysis in aqueous ytterbium triflate solution

Tetrahedron Letters

Volumn 39, Issue 46, 1998, Pages 8549-8552

  Beaton, Martin ^a   Gani, David ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,6 EPOXY 2,4 BIS(BENZYLOXYCYCLOPHEXANE); ALIPHATIC AMINE; AMMONIA; INOSITOL MONOPHOSPHATASE; QUINIC ACID; UNCLASSIFIED DRUG; YTTERBIUM;

DRUG MECHANISM; ENZYME INHIBITION; HYDROLYSIS; METAL BINDING; QUANTITATIVE DIAGNOSIS; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032512031     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01909-1     Document Type: Article

References (13)

1. 1. Gani, D., Downes, C. P., Batty, I. and Bramham, J. (1993) Biochim. Biophys. Acta 1177, 253-269; Leech, A. P., Baker, G. R., Shute, J. K., Cohen, M. A. and Gani, D. (1993) Eur. J. Biochem. 212, 693-704.
2. 1. Gani, D., Downes, C. P., Batty, I. and Bramham, J. (1993) Biochim. Biophys. Acta 1177, 253-269; Leech, A. P., Baker, G. R., Shute, J. K., Cohen, M. A. and Gani, D. (1993) Eur. J. Biochem. 212, 693-704.
3. 2. a) Pollack, S. J., Atack, J. R., Knowles, M. R., McAllister, G., Ragan, C. I., Baker, R., Fletcher, S. R., Iverson, L. L. and Broughton, H. B. (1994) Proc. Natl. Acad. Sci. USA 91, 5766-5770.
4. b) Bone, R., Frank, L., Springer, J. P. and Atack, J. R. (1994) Biochemistry 33, 9468-9476.
5. 3. Cole, A. G. and Gani, D. (1994) J. Chem. Soc., Chem. Commun. 1139-1141; Wilkie, J., Cole, A. G. and Gani, D. (1995) J. Chem. Soc., Perkin Trans. 1 2709-2727.
6. 3. Cole, A. G. and Gani, D. (1994) J. Chem. Soc., Chem. Commun. 1139-1141; Wilkie, J., Cole, A. G. and Gani, D. (1995) J. Chem. Soc., Perkin Trans. 1 2709-2727.
7. 4. Schulz, J., Wilkie, J., Lightfoot, P., Rutherford, T. and Gani, D. (1995) J. Chem. Soc., Chem. Commun. 2353-2356.
8. 5. Schulz, J. and Gani, D. (1997) J. Chem. Soc., Perkin Trans. 1 657-670 and references cited therein.
9. 6. Schulz, J. and Gani, D. (1997) Tetrahedron Lett. 38, 111-114 and references cited therein.
10. 7. Carre, M. C., Houmounou, J. P. and Caubere, P. (1985) Tetrahedron Lett. 26, 3107-3110.
11. 8. Chini, M., Crotti, P. and Macchia, F. (1990) Tetrahedron Lett. 31, 4661-4664.
12. 9. Chini, M., Crotti, P. and Macchia, F. (1994) Tetrahedron Lett. 35, 433-436.
13. 8NaP: 758.2859. Found 758.2880. Note: Compound 12 (R = Me) exists as two N-methyl benzylureathane rotomers.