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Abstract:

Benzoylation ofD-glycero-D-gulo-heptono-1,4-lactone afforded 2,3,5,6,7-penta-O-benzoyl-D-glycero-D-gulo-heptono-1,4-lactone, which, by 3-deoxygenation, gave 2,5,6,7-tetra-O-benzoyl-3-deoxy-D-gluco-heptono-1,4-lactone (4) in 80% overall yield. In a similar way, 2,5,6,7-tetra-O-acetyl-3-deoxy-D-gluco-heptono-1,4-lactone was prepared. Disiamylborane reduction of compound 4 gave crystalline 2,5,6,7-tetra-O-benzoyl-3-deoxy-β-D-gluco-heptofuranose (6), which was acetylated to give crystalline 1-O-acetyl-2,5,6,7-tetra-O-benzoyl-3-deoxy-β-D-gluco-heptofuranose (7). Upon treatment of 6 with diazomethane-boron trifluoride etherate, methyl 2,5,6,7-tetra-O-benzoyl-3-deoxy-β-D-gluco-heptofuranoside (8) was obtained. From the reaction mixture, the benzoylated β,β′-furanosyl disaccharide 11 was isolated. A higher yield (90%) of 8 was obtained by treatment of 7 with methanol and tin(IV) chloride. On O-debenzoylation of 8, methyl 3-deoxy-β-D-gluco-heptofuranoside was obtained. Compound 11 was the sole product (82% yield) when 6 was treated with boron trifluoride-etherate in dichloromethane. O-Debenzoylation of 11 afforded crystalline 3-deoxy-β-D-gluco-heptofuranosyl 3-deoxy-β-D-gluco-heptofuranoside. O-Debenzoylation of 6 with sodium methoxide in chloroform afforded crystalline 3-deoxy-D-gluco-heptose, whose tautomeric equilibrium was studied by 13C-n.m.r. spectroscopy. © 1987.

Registro:

Documento: Artículo
Título:Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose
Autor:Jeroncic, L.O.; Cirelli, A.F.; de Lederkremer, R.M.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires. Ciudad Universitaria, Pabellón 2, piso 3, 1428 Buenos Aires, Argentina
Año:1987
Volumen:167
Número:C
Página de inicio:175
Página de fin:186
DOI: http://dx.doi.org/10.1016/0008-6215(87)80277-X
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v167_nC_p175_Jeroncic

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Citas:

---------- APA ----------
Jeroncic, L.O., Cirelli, A.F. & de Lederkremer, R.M. (1987) . Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose. Carbohydrate Research, 167(C), 175-186.
http://dx.doi.org/10.1016/0008-6215(87)80277-X
---------- CHICAGO ----------
Jeroncic, L.O., Cirelli, A.F., de Lederkremer, R.M. "Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose" . Carbohydrate Research 167, no. C (1987) : 175-186.
http://dx.doi.org/10.1016/0008-6215(87)80277-X
---------- MLA ----------
Jeroncic, L.O., Cirelli, A.F., de Lederkremer, R.M. "Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose" . Carbohydrate Research, vol. 167, no. C, 1987, pp. 175-186.
http://dx.doi.org/10.1016/0008-6215(87)80277-X
---------- VANCOUVER ----------
Jeroncic, L.O., Cirelli, A.F., de Lederkremer, R.M. Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose. Carbohydr. Res. 1987;167(C):175-186.
http://dx.doi.org/10.1016/0008-6215(87)80277-X