A straightforward route to N-acetyl-D-glucosamine-derived C-β-D-glycosyl synthons

Tetrahedron Letters

Volumn 37, Issue 14, 1996, Pages 2341-2344

  Petrušová, Mária ^a   BeMiller, James N ^b   Petruš, Ladislav ^a  

^a INSTITUTE OF CHEMISTRY   (Slovakia)

^b PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCOSAMINE DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029994585     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00280-8     Document Type: Article

References (40)

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25. Surprisingly, C-glycosylnitromethanes are resistant to the Nef reaction commonly used for transformation of a nitro to a carbonyl group. A procedure for their simple conversion to C-glycosylcarboxylic (2,6-anhydroaldonic) acids has been announced: Köll P.; Dromowicz, H. Abstr. Eur. Carbohydr. Symp., 6th, Edinburgh, 1991, B56.
26. Ozonolysis of sodium nitronate forms of sugar nitro derivatives, some of which also contain the acetamido functionality, to carbonyl derivatives has been previously described, (a) Lattová, E.; Petrušová, M.; Petruǎ, L. Chem. Pap. 1991, 45, 823-827.
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30. Ozonolysis of silyl nitronates of C-glycosylnitromethanes, not containing an acetamido functionality, to C-glycosylformaldehydes has also been described: Martin, O. R.; Khamis, F. E.; Rao, S. P. Tetrahedron Lett. 1989, 30, 6143-6146.
31. Optimized excess for the conditions used. An excess of NaOH was necessary to assure complete disappearance of starting 2 (cf. note 12), as a part of 3 formed was subsequently oxidized to acid 4, which consumed the extra base.
32. 13C NMR signal of COONa of the Na salt of 4 was observed at δ 178.3 ppm.
33. 3 (a side product of the ozonolysis of sodium nitronates) and acid 4. If 2 was not completely reacted in the ozonolysis step, it contaminated intermediate 5 and the other products, from which it was difficult to separate by both recrystallization and column chromatography.
34. 4 used as catalyst had to be added to the ice-water mixture; otherwise only underacetylated species were isolated.
35. 10: C, 47.76; H, 5.51; N, 6.96. Found: C, 47.39; H, 5.58; N, 6.79.
36. A series of model compounds with the acetamido functionality was prepared to support the interpretation (to be published separately). It was indicated that a strain influencing the acetyl group to be eliminated had to be present. In this case, a parallel interaction with an unbonded electron pair of the ring oxygen atom seemed to provide the necessary strain.
37. 3, e.g., according to: Sowden J. C.; Fischer, H. O. L. J. Am. Chem. Soc., 1947, 69, 1048-1050.
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39. 7: C, 43.16; H, 6.52; N, 10.07. Found: C, 42.86; H, 6.77; N, 9.84.
40. Petruš, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197-200.