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Homologation of hexopyranosides: use of differential Overhauser nuclear effect, and homo- and heteronuclear correlations of chemical shift for characterization of the 1,6-anhydro-4-O-benzoyl-2,3-didesoky-3-C-trifluoroacetamidomethyl-{beta}-D-m = ethyl ribopyranoside (16a); Homologacao de hexopiranosideos: utilizacao de efeito nuclear overhauser diferencial e de correlacoes homo e heteronuclear de deslocamentos quimicos para a caracterizacao do 1,6-anidro-4-O-benzoil-2,3-didesoxi-3-C- trifluoroacetamidometil-{beta}-D-ribo piranosideo de metila (16a)

Miscellaneous:

Abstract

The discovery of ramified sugars as various antibiotics constituents, leads to the development of various preparation technologies. In the framework of hexa pyranose analogues synthesis, the 1,6-anhydride -16a was one of the byproducts obtained in the attempt of bromide -16 derivative transformation in the iodate -6-1 derivative. The bromide -16 derivative was treated with 2 equivalents of Bu{sub 4} N I during 24 hours, acetonitrile reflux. 3 parts of 2 Bu{sub 4} N I equivalents were added each 24 hours. A unique pure substance was obtained from the formed products mixture, which the structural determination was proposed in accordance with: 1) disappearing of the C-13 signal and the two protons from the anomeric methoxy group, and 2) registering of the molecular ion with m/z 359D, corresponding to the loss of 94D (Br + C H{sub 3}), from the -16 (M{sup +}., m/z 453D). The 1,6-anhydride -16a structure was confirmed by experiments on homo- and heteronuclear correlations of chemical shifts (COSY H-H and COSY C-H), and by spectroscopy using the differential Overhauser nuclear effect. The spectrum obtained by C-H correlation identified the singlet at 5.65 ppm as due to the H-1 ([C-1 x H-1]) 2 refs., 6 figs.
Authors:
Souza Filho, J D; Silva, L.G. Fonseca e; Oliveira, A Braga de; Alves, R Jose; [1]  Lukacs, G [2] 
  1. Minas Gerais Univ., Belo Horizonte, MG (Brazil)
  2. Centre National de la Recherche Scientifique (CNRS), 91 - Gif-sur-Yvette (France). Inst. de Chimie des Substances Naturelles
Publication Date:
Dec 31, 1991
Product Type:
Miscellaneous
Report Number:
CONF-9105459-
Reference Number:
SCA: 665100; 664200; 400101; PA: AIX-29:045913; EDB-98:091420; SN: 98001998991
Resource Relation:
Conference: 3. meeting of nuclear magnetic resonance users, 3. Encontro de usuarios de ressonancia magnetica nuclear, Buzios (Brazil), 14-18 May 1991; Other Information: DN: 2 refs., 6 figs.; PBD: 1991; Related Information: Is Part Of Proceedings of the 3. Meeting of nuclear magnetic resonance users; PB: 425 p.; Anais do 3. encontro de usuarios de ressonancia magnetica nuclear
Subject:
66 PHYSICS; 40 CHEMISTRY; ANTIBIOTICS; CARBOHYDRATES; CHEMICAL PREPARATION; NUCLEAR MAGNETIC RESONANCE; OVERHAUSER EFFECT; SACCHAROSE; SYNTHESIS
OSTI ID:
636807
Research Organizations:
Associacao de Usuarios de Ressonancia Magnetica Nuclear, Rio de Janeiro, RJ (Brazil)
Country of Origin:
Brazil
Language:
Portuguese
Other Identifying Numbers:
TRN: BR98E1468045913
Availability:
Available from the Library of the Brazilian Nuclear Energy Commission, Rio de Janeiro
Submitting Site:
BRN
Size:
pp. 413-418
Announcement Date:

Miscellaneous:

Citation Formats

Souza Filho, J D, Silva, L.G. Fonseca e, Oliveira, A Braga de, Alves, R Jose, and Lukacs, G. Homologation of hexopyranosides: use of differential Overhauser nuclear effect, and homo- and heteronuclear correlations of chemical shift for characterization of the 1,6-anhydro-4-O-benzoyl-2,3-didesoky-3-C-trifluoroacetamidomethyl-{beta}-D-m = ethyl ribopyranoside (16a); Homologacao de hexopiranosideos: utilizacao de efeito nuclear overhauser diferencial e de correlacoes homo e heteronuclear de deslocamentos quimicos para a caracterizacao do 1,6-anidro-4-O-benzoil-2,3-didesoxi-3-C- trifluoroacetamidometil-{beta}-D-ribo piranosideo de metila (16a). Brazil: N. p., 1991. Web.
Souza Filho, J D, Silva, L.G. Fonseca e, Oliveira, A Braga de, Alves, R Jose, & Lukacs, G. Homologation of hexopyranosides: use of differential Overhauser nuclear effect, and homo- and heteronuclear correlations of chemical shift for characterization of the 1,6-anhydro-4-O-benzoyl-2,3-didesoky-3-C-trifluoroacetamidomethyl-{beta}-D-m = ethyl ribopyranoside (16a); Homologacao de hexopiranosideos: utilizacao de efeito nuclear overhauser diferencial e de correlacoes homo e heteronuclear de deslocamentos quimicos para a caracterizacao do 1,6-anidro-4-O-benzoil-2,3-didesoxi-3-C- trifluoroacetamidometil-{beta}-D-ribo piranosideo de metila (16a). Brazil.
Souza Filho, J D, Silva, L.G. Fonseca e, Oliveira, A Braga de, Alves, R Jose, and Lukacs, G. 1991. "Homologation of hexopyranosides: use of differential Overhauser nuclear effect, and homo- and heteronuclear correlations of chemical shift for characterization of the 1,6-anhydro-4-O-benzoyl-2,3-didesoky-3-C-trifluoroacetamidomethyl-{beta}-D-m = ethyl ribopyranoside (16a); Homologacao de hexopiranosideos: utilizacao de efeito nuclear overhauser diferencial e de correlacoes homo e heteronuclear de deslocamentos quimicos para a caracterizacao do 1,6-anidro-4-O-benzoil-2,3-didesoxi-3-C- trifluoroacetamidometil-{beta}-D-ribo piranosideo de metila (16a)." Brazil.
@misc{etde_636807,
title = {Homologation of hexopyranosides: use of differential Overhauser nuclear effect, and homo- and heteronuclear correlations of chemical shift for characterization of the 1,6-anhydro-4-O-benzoyl-2,3-didesoky-3-C-trifluoroacetamidomethyl-{beta}-D-m = ethyl ribopyranoside (16a); Homologacao de hexopiranosideos: utilizacao de efeito nuclear overhauser diferencial e de correlacoes homo e heteronuclear de deslocamentos quimicos para a caracterizacao do 1,6-anidro-4-O-benzoil-2,3-didesoxi-3-C- trifluoroacetamidometil-{beta}-D-ribo piranosideo de metila (16a)}
author = {Souza Filho, J D, Silva, L.G. Fonseca e, Oliveira, A Braga de, Alves, R Jose, and Lukacs, G}
abstractNote = {The discovery of ramified sugars as various antibiotics constituents, leads to the development of various preparation technologies. In the framework of hexa pyranose analogues synthesis, the 1,6-anhydride -16a was one of the byproducts obtained in the attempt of bromide -16 derivative transformation in the iodate -6-1 derivative. The bromide -16 derivative was treated with 2 equivalents of Bu{sub 4} N I during 24 hours, acetonitrile reflux. 3 parts of 2 Bu{sub 4} N I equivalents were added each 24 hours. A unique pure substance was obtained from the formed products mixture, which the structural determination was proposed in accordance with: 1) disappearing of the C-13 signal and the two protons from the anomeric methoxy group, and 2) registering of the molecular ion with m/z 359D, corresponding to the loss of 94D (Br + C H{sub 3}), from the -16 (M{sup +}., m/z 453D). The 1,6-anhydride -16a structure was confirmed by experiments on homo- and heteronuclear correlations of chemical shifts (COSY H-H and COSY C-H), and by spectroscopy using the differential Overhauser nuclear effect. The spectrum obtained by C-H correlation identified the singlet at 5.65 ppm as due to the H-1 ([C-1 x H-1]) 2 refs., 6 figs.}
place = {Brazil}
year = {1991}
month = {Dec}
}