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b. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1997, 53, 5643; 1996, 52, 4527.
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5
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0001926444
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Gross, E.; Meienhofer, J. Eds. Academic Press, New York
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b. For a review of the application of the Merrifield resin in solid phase peptide synthesis, see: Barany, G.; Merrifield, R. B. in The Peptides, 2, 1-284, 1980, Gross, E.; Meienhofer, J. Eds. Academic Press, New York.
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3. See for example: a. Chem. Rev. 1997, 97 (2);
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b. Borman, S. C&EN, 1997, Feb. 24, 43;
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c. Acc. Chem. Res. 1996, 29 (3), 111 ;
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d. Terrett, N. K.; Gardner, M.; Gordon, D. W.: Kobyleski, R. J.; Steele, J. Tetrahedron 1995, 51, 8135.
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11
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0028088788
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5. For an example of transesterification with release of the new ester from the resin, see: Frenette, R.; Friesen, R. W.; Tetrahedron Lett. 1994, 35, 9177.
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6. Davis, F. A.; Haque, M. S.; Ulatowski, T.G.; Towson, J. C. J. Org. Chem. 1986, 51, 2402.
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0010662439
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7. Terashima, S.; Hayashi, M.; Tseng, C. C.; Koga, K. Tetrahedron Lett. 1978, 1763.
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Terashima, S.1
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14
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0010742670
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Patent, US 5,324,483,1994
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8. For an example of a Grignard reaction on an N-methoxy amide bound to a solid support, see: Reynolds Cody, D. M.; Hobbs DeWitt, S.H.; Hodges, J. C.; Kiely, J. S.; Moos, W. M.; Pavia, M. R.; Roth, B. D.; Schroeder, M. C.; Stankovic, C. J.; Patent, US 5,324,483,1994.
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Reynolds Cody, D.M.1
Hobbs DeWitt, S.H.2
Hodges, J.C.3
Kiely, J.S.4
Moos, W.M.5
Pavia, M.R.6
Roth, B.D.7
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Stankovic, C.J.9
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15
-
-
0010703881
-
-
note
-
9. For an amidation reaction of an ester-bound substrate, see ref. 8.
-
-
-
-
16
-
-
0010666646
-
-
note
-
10. Quinic acid N-benzylamide was synthesized as follows: (Equation Presented)
-
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17
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0000865359
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11. Lal, B.; Pramanik, B. N.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett, 1977, 1977
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Lal, B.1
Pramanik, B.N.2
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Bose, A.K.4
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18
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0029011229
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12. For examples of Mitsunobu reactions on solid support, see: a. Rano, T. A.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 3789;
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0029090312
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b. Krchnak, V.; Flegelova, Z.; Weichsel, A. S.; Lebl, M. Tetrahedron Lett. 1995, 36, 6193.
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Krchnak, V.1
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20
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0028127424
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13. For examples of enolate alkylation of amides, see: a. Moon, H.-S; Schore, N. E.: Kurth, M. J.; Tetrahedron Lett. 1994, 35, 8915;
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Moon, H.-S.1
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Kurth, M.J.3
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22
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0000590383
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14. The presence of pyridine during ozonolysis is considered to play a key role in protecting the resin from oxidation. For the use of pyridine in ozonolysis, see: Slomp, Jr.; Johnson, J. L. J. Am. Chem. Soc. 1958, 80, 915.
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23
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0031562046
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15. Sylvain, C.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 1043; see also Fréchet, J. M.; Schuerch, C. Carbohydr. Res. 1972, 22, 399.
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Sylvain, C.1
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33748519998
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15. Sylvain, C.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 1043; see also Fréchet, J. M.; Schuerch, C. Carbohydr. Res. 1972, 22, 399.
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Fréchet, J.M.1
Schuerch, C.2
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25
-
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0010703650
-
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note
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16. The reaction has not been optimized since ∼20% unreduced aldehyde was also present.
-
-
-
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27
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0028053596
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18. Yu, K.-L; Deshpande, M. S. and Vyas, D. M. Tetrahedron Lett. 1994, 35, 8919
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Vyas, D.M.3
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28
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-
0029030381
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-
see also ref. 18; and references cited therein
-
19. For examples of Heck reactions on solid support, see: Hiroshige, M.; Hauske, J. R.; Zhou, P.; Tetrahedron Lett. 1995, 36, 4567; see also ref. 18; and references cited therein.
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Hiroshige, M.1
Hauske, J.R.2
Zhou, P.3
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29
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0010703104
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note
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20. The purity of the products was ascertained by HPLC (>90%) as well as by comparison with authentic samples.
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