Abstract:
Trans-opening of the 2,3-anhydro-6-deoxy-4-O-methyl-α-D-allopyranoside with lithium bromide yields the altro and gluco regioisomers methyl 2-bromo- 2,6-dideoxy-4-O-methyl-α-D-altropyranoside and methyl 2-bromo-3,6-dideoxy- 4-O-methyl-α-D-glycopyranoside which can be hydrolysed to give the sugar precursors 2-bromo-2,6-dideoxy-4-O-methyl-α/β-D-altropyranose and 3-bromo- 3,6-dideoxy-4-O-methyl-D-glucopyranose. Under Mitsunobu conditions the altro compound yields the first 1,3-anhydro-altrose derivative. In case of the gluco derivative alkaline treatment does not give a 1,3-anhydro-glucose derivative but the 2,6-dideoxy-altrose via intermediate 2,3-epoxide formation. Methanolysis and reductive debromination under photolytic initiation were studied.
Registro:
Documento: |
Artículo
|
Título: | Synthesis of thromboxane A2 models from glucose |
Autor: | Cirelli, A.F.; Mohn, H.; Thiem, J. |
Filiación: | Depto. de Quimica Orgánica, Ciudad Universitaria, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina Organisch-Chemisches Institut, Westfälische Wilhelms-Univ., Orléansring 23, D-48149 Münster, Germany Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany
|
Palabras clave: | 1.3-Anhydro-α-D-altropyranoside; 2,6- dideoxy; 2.6-Dioxabicyclo[3.1.1]heptanes; Model compounds; Thromboxane; glucose; pyranoside; sugar; thromboxane a2; article; debromination; isomer; photolysis; priority journal; reaction analysis; synthesis |
Año: | 1997
|
Volumen: | 303
|
Número: | 4
|
Página de inicio: | 417
|
Página de fin: | 422
|
DOI: |
http://dx.doi.org/10.1016/S0008-6215(97)00183-3 |
Título revista: | Carbohydrate Research
|
Título revista abreviado: | CARBOHYDR. RES.
|
ISSN: | 00086215
|
CODEN: | CRBRA
|
CAS: | glucose, 50-99-7, 84778-64-3; thromboxane A2, 57576-52-0
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v303_n4_p417_Cirelli |
Referencias:
- Hamberg, M., Svenson, J., Samuelson, B., (1975) Proc. Natl. Acad. Sci. USA, 72, pp. 2994-2998
- Needleman, R., Moncada, S., Bunting, S., Vane, J.R., Hamberg, M., Samuelson, B., (1976) Nature, 261, pp. 558-560
- Corey, E.J., Shibasaki, M., Knolle, J., Sugahara, T., (1977) Tetrahedron Lett., pp. 785-788
- Hanessian, S., Lavallee, P., (1997) Can. J. Chem., 55, pp. 562-565
- Hanessian, S., Lavallee, P., (1981) Can. J. Chem., 59, pp. 870-877
- Newton, R.F., Roberts, S.M., Taylor, J.K., (1984) Synthesis, pp. 449-478. , and literature cited therein
- Fried, J., Hallinan, E.A., Szwedo M.J., Jr., (1984) J. Am. Chem. Soc., 106, pp. 3871-3872
- Bhagwat, S.S., Hamann, P.R., Still, W.C., (1985) Tetrahedron Lett., 26, pp. 1955-1958
- Bhagwat, S.S., Hamann, P.R., Still, W.C., Bunting, S., Fitzpatrick, F.A., (1985) Nature, 315, pp. 511-513
- Bhagwat, S.S., Hamann, P.R., Still, W.C., (1985) J. Am. Chem. Soc., 107, pp. 6372-6376
- Ito, H., Eby, R., Kramer, S., Schuerch, C., (1980) Carbohydr. Res., 86, pp. 193-202
- Varma, A.J., Schuerch, C., (1981) J. Org. Chem., 46, pp. 799-803
- Kong, F., Schuerch, C., (1983) Carbohydr. Res., 112, pp. 141-147
- Good, F., Schuerch, C., (1984) Carbohydr. Res., 125, pp. 165-171
- Wu, X., Kong, F., Lu, D., Zhang, P., (1992) Carbohydr. Res., 224, pp. 75-87
- Yang, C., Kong, F., Cao, L., (1992) J. Carbohydr. Chem., 11, pp. 379-395
- Gan, Z., Kong, F., (1995) Carbohydr. Res., 270, pp. 211-215
- Richtmyer, N.K., Hudson, C.S., (1941) J. Am. Chem. Soc., 63, pp. 1727-1731
- Paulsen, H., Sinnwell, V., (1978) Chem. Ber., 111, pp. 879-889
- Purdie, T., Irvine, J.C., (1903) J. Chem. Soc., 83, pp. 1021-1037
- Lemieux, R.U., Fraga, E., Watanabe, K.A., (1968) Can. J. Chem., 446, pp. 61-69
- Thiem, J., Karl, H., Ellermann, U., (1979) Chem. Ber., 112, pp. 3139-3148
- Fürst, A., Plattner, P.A., (1949) Helv. Chim. Acta, 32, pp. 275-283
- Bourne, E.J., Peat, S., (1950) Advan. Carbohydr. Chem., 5, pp. 145-190
- Winstein, S., Lucas, H.J., (1939) J. Am. Chem. Soc., 61, pp. 1576-1581
- Kadesch, R.G., (1946) J. Am. Chem. Soc., 68, pp. 41-45
- Fuchs, E.-F., Horton, D., Weckerle, W., (1977) Carbohydr. Res., 57, pp. C36-C39
- Adiwidjaja, G., Meyer, B., Paulsen, H., Thiem, J., (1979) Tetrahedron, 35, pp. 373-384
- Mitsunobu, O., (1981) Synthesis, pp. 1-28
- Khetrapal, C.L., Kunwar, A.C., Saupe, A., (1973) Mol. Phys., 25, pp. 1405-1413
- Sternhell, S., (1969) Quart. Rev. Chem. Soc., 23, pp. 236-270
- Kotowycz, G., Lemieux, R.U., (1973) Chem. Rev., 73, pp. 669-698
- Wiberg, K.B., Lampman, G.M., Ciula, R.P., Connor, D.S., Schertler, P., Lavanish, J., (1965) Tetrahedron, 21, pp. 2749-2769
- Tori, K., Ohtsuru, M., Hata, Y., Tanida, H., (1968) J. Chem. Soc., Chem. Commun., p. 1096
- Krebs, H.A., Hensleit, K., (1932) Hoppe-seyler's Z. Physiol. Chem., 210, pp. 33-66
- Burch, R.M., Mais, D.E., Saussy, D.L., Halushka, P.V., (1985) Proc. Natl. Acad. Sci. USA, 82, pp. 7434-7438
- Sprague, P.W., Heikes, J.E., Gougoutas, J.Z., Malley, M.F., Harris, D.N., Greenberg, R., (1985) J. Med. Chem., 28, pp. 1580-1590
- Cerny, M., Stanek J., Jr., (1977) Advan. Carbohydr. Chem. Biochem., 34, pp. 23-177
- Atkinson, R.F., Bruice, T.C., (1974) J. Am. Chem. Soc., 96, pp. 819-825
Citas:
---------- APA ----------
Cirelli, A.F., Mohn, H. & Thiem, J.
(1997)
. Synthesis of thromboxane A2 models from glucose. Carbohydrate Research, 303(4), 417-422.
http://dx.doi.org/10.1016/S0008-6215(97)00183-3---------- CHICAGO ----------
Cirelli, A.F., Mohn, H., Thiem, J.
"Synthesis of thromboxane A2 models from glucose"
. Carbohydrate Research 303, no. 4
(1997) : 417-422.
http://dx.doi.org/10.1016/S0008-6215(97)00183-3---------- MLA ----------
Cirelli, A.F., Mohn, H., Thiem, J.
"Synthesis of thromboxane A2 models from glucose"
. Carbohydrate Research, vol. 303, no. 4, 1997, pp. 417-422.
http://dx.doi.org/10.1016/S0008-6215(97)00183-3---------- VANCOUVER ----------
Cirelli, A.F., Mohn, H., Thiem, J. Synthesis of thromboxane A2 models from glucose. CARBOHYDR. RES. 1997;303(4):417-422.
http://dx.doi.org/10.1016/S0008-6215(97)00183-3