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Volumn 55, Issue 12, 1990, Pages 3772-3787

Glycosyl α-Amino Acids via Stereocontrolled Buildup of a Penaldic Acid Equivalent. A Novel Synthetic Approach to the Nucleosidic Component of the Polyoxins and Related Substances

Author keywords

[No Author keywords available]

Indexed keywords

THYMINE POLYOXIN C;

EID: 0025072488     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00299a017     Document Type: Article
Times cited : (126)

References (69)
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    • Other synthetic applications of 4 and its antipode include the following. The sphingosine bases
    • Other synthetic applications of 4 and its antipode include the following. The sphingosine bases: (a) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A. J. Chem. Soc., Chem. Commun. 1988, 10.
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    • Prepared in two steps (37% overall distilled yield on a 5-mol scale) from acrolein by a route analogous to that reported for propiolaldehyde diethyl acetal: Le Coq, A.; Gorgues, A. In Organic Syntheses; Coates, R. M., E.; Wiley: New York, 1979; Vol. 59, pp 10–15.
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    • However, we found it more convenient and economical to use KOH as the base for the double dehydrohalogenation step rather than the 300 mol % of Bu4N+HSO4’ reported in the Organic Syntheses procedure
    • However, we found it more convenient and economical to use KOH as the base for the double dehydrohalogenation step rather than the 300 mol % of Bu4N+HSO4’ reported in the Organic Syntheses procedure. Cf.: Sheehan, J. C.; Robinson, C. A. J. Am. Chem. Soc. 1949, 71, 1436.
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    • Chemical evidence for the Z-olefin geometry in 10 was gleaned at this stage from an attempted high temperature 13C NMR experiment wherein it was observed that prolonged heating of a C6D6 solution of 10 at 60 °C for a period of 4–5 h resulted in spontaneous cyclization to the dihydrofurans 11 and 12. Cf
    • Chemical evidence for the Z-olefin geometry in 10 was gleaned at this stage from an attempted high temperature 13C NMR experiment wherein it was observed that prolonged heating of a C6D6 solution of 10 at 60 °C for a period of 4–5 h resulted in spontaneous cyclization to the dihydrofurans 11 and 12. Cf.: Seyfath, H. E. Chem. Ber. 1968, 101, 619.
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    • The 13C chemical shift of the anomeric carbons in these compounds was, however, indicative of the spacial relationship between the substituents at C-4’ and C-5’ with the respective anomeric carbons of 15 and 16 (both 4‘,5’-trans disubstituted) resonating 7.8 and 5.6 ppm downfield of the anomeric carbon in 17 (4/,5/-cis disubstituted). Cf
    • The 13C chemical shift of the anomeric carbons in these compounds was, however, indicative of the spacial relationship between the substituents at C-4’ and C-5’ with the respective anomeric carbons of 15 and 16 (both 4‘,5’-trans disubstituted) resonating 7.8 and 5.6 ppm downfield of the anomeric carbon in 17 (4/,5/-cis disubstituted). Cf.: Ritchie, R. G. S.; Cyr, N.; Korsch, B.; Koch, H. J.; Perlin, A. S. Can. J. Chem. 1975, 53, 1424.
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    • We did not experience any difficulty with this oxidation, performed here in aqueous acetone, due to the formation of (inactive) lower valent ruthenium carboxylates. Compare
    • We did not experience any difficulty with this oxidation, performed here in aqueous acetone, due to the formation of (inactive) lower valent ruthenium carboxylates. Compare: Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
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    • Prepared by mild esterification of 38 using amberlyst-15 as an acid catalyst
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    • Prepared by mild esterification of 38 using amberlyst-15 as an acid catalyst (Petrini, M.; Ballini, R.; Marcantoni, E.; Rosini, G. Synth. Commun. 1988, 18, 847) followed by standard O-acetylation (Ac20 + Pyridine).
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    • Preliminary indication that the benzyloxycarbonyl group would survive these acidic nucleosidation conditions was available to us. See: Paulsen, H.; Brieden, M.; Benz, G. Justus Leibigs Ann. Chem. 1987, 565.
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    • The question of just what factors govern endocyclic versus exocyclic glycosyl cleavage in sugars is of general interest, but a detailed understanding of the problem remains somewhat elusive
    • The question of just what factors govern endocyclic versus exocyclic glycosyl cleavage in sugars is of general interest, but a detailed understanding of the problem remains somewhat elusive. (Of.: Cosse-Barbi, A.; Watson, D. G.; Dubois, J. E. Tetrahedron Lett. 1989, 163.
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    • We thank Professor Frank Hauser (SUNY/Albany) for alerting us to the advantages of substituting trimethylamine-N-oxide as the carrier oxidant in this reaction
    • We thank Professor Frank Hauser (SUNY/Albany) for alerting us to the advantages of substituting trimethylamine-N-oxide as the carrier oxidant in this reaction. Cf. Ray, R.; Matteson, D. S. Tetrahedron Lett. 1980, 449.
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    • A similar problem was encountered by Rosenthal and Cliff d their work on the synthesis of polyoxin analogues having the 1 fluoroacetamido glycine methyl ester moiety appended to C-3
    • A similar problem was encountered by Rosenthal and Cliff d their work on the synthesis of polyoxin analogues having the 1 fluoroacetamido glycine methyl ester moiety appended to C-3, see: senthal, A.; Cliff, B. Carbohydr. Res. 1980, 79, 63.
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    • The numbering system used in this paper corresponds to the current CA index names for substructures i—iii. For details
    • American Chemical Society: Washington, DC
    • The numbering system used in this paper corresponds to the current CA index names for substructures i—iii. For details, see: Chemical Abstracts Service Index Guide; American Chemical Society: Washington, DC, 1989.
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