Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose

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-...

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Autores principales: Jeroncic, L.O., Cirelli, A.F., de Lederkremer, R.M.
Formato: JOUR
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00086215_v167_nC_p175_Jeroncic
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling todo:paper_00086215_v167_nC_p175_Jeroncic2023-10-03T14:06:25Z Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose Jeroncic, L.O. Cirelli, A.F. de Lederkremer, R.M. 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. Fil:Jeroncic, L.O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:de Lederkremer, R.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00086215_v167_nC_p175_Jeroncic
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
description 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.
format JOUR
author Jeroncic, L.O.
Cirelli, A.F.
de Lederkremer, R.M.
spellingShingle Jeroncic, L.O.
Cirelli, A.F.
de Lederkremer, R.M.
Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose
author_facet Jeroncic, L.O.
Cirelli, A.F.
de Lederkremer, R.M.
author_sort Jeroncic, L.O.
title Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose
title_short Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose
title_full Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose
title_fullStr Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose
title_full_unstemmed Synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose
title_sort synthesis of crystalline derivatives of 3-deoxy-d-gluco-heptofuranose
url http://hdl.handle.net/20.500.12110/paper_00086215_v167_nC_p175_Jeroncic
work_keys_str_mv AT jeronciclo synthesisofcrystallinederivativesof3deoxydglucoheptofuranose
AT cirelliaf synthesisofcrystallinederivativesof3deoxydglucoheptofuranose
AT delederkremerrm synthesisofcrystallinederivativesof3deoxydglucoheptofuranose
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