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Abstract:

The synthesis of the trisaccharide α-d-Glcp-(1→3)-α-d- Galf-(1→2)-l-Rhap (3) constituent of Streptococcus pneumonia 22F was achieved with complete diastereoselectivity. This is the first example of a synthesis of an internal α-d-Galf containing oligosaccharide of a pathogen microorganism. Allyl α-d-galactofuranoside, used as novel precursor of the internal Galf, allowed the introduction of an orthogonal group at O-3. The trichloroacetimidate method was used for the construction of 1,2-cis-α-d-galactofuranosyl linkage. The influence of the 3-O-substituent (PMB, Bz, PFBz, PMBz, TIPS) was evaluated in benzylated galactofuranosyl trichloroacetimidate donors in terms of yield and selectivity of α-d-Galf-(1→2)-α-l-Rhap product as well as donor rearrangement by-product. Complete stereoselectivity was observed with all protecting groups used in the Galf donor, but the 3-O-benzoyl substitution gave the best yield. Protective groups were also evaluated in the rhamnoside acceptor, benzyl substitution was a requirement for complete stereoselectivity.

Registro:

Documento: Artículo
Título:Synthesis of α-d-Glcp-(1→3)-α-d-Galf-(1→2)-α-l- Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis α-d-galactofuranosylation
Autor:Gola, G.; Gallo-Rodriguez, C.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria Pabellón II, 1428 Buenos Aires, Argentina
Idioma: Inglés
Palabras clave:Diastereo-selectivity; Novel precursors; Orthogonal groups; Protecting group; Protective group; Streptococcus pneumoniae; Trichloroacetimidate; Stereoselectivity
Año:2014
Volumen:4
Número:7
Página de inicio:3368
Página de fin:3382
DOI: http://dx.doi.org/10.1039/c3ra45658g
Título revista:RSC Advances
Título revista abreviado:RSC Adv.
ISSN:20462069
CODEN:RSCAC
Registro:http://digital.bl.fcen.uba.ar/collection/paper/document/paper_20462069_v4_n7_p3368_Gola

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Citas:

---------- APA ----------
Gola, G. & Gallo-Rodriguez, C. (2014) . Synthesis of α-d-Glcp-(1→3)-α-d-Galf-(1→2)-α-l- Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis α-d-galactofuranosylation. RSC Advances, 4(7), 3368-3382.
http://dx.doi.org/10.1039/c3ra45658g
---------- CHICAGO ----------
Gola, G., Gallo-Rodriguez, C. "Synthesis of α-d-Glcp-(1→3)-α-d-Galf-(1→2)-α-l- Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis α-d-galactofuranosylation" . RSC Advances 4, no. 7 (2014) : 3368-3382.
http://dx.doi.org/10.1039/c3ra45658g
---------- MLA ----------
Gola, G., Gallo-Rodriguez, C. "Synthesis of α-d-Glcp-(1→3)-α-d-Galf-(1→2)-α-l- Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis α-d-galactofuranosylation" . RSC Advances, vol. 4, no. 7, 2014, pp. 3368-3382.
http://dx.doi.org/10.1039/c3ra45658g
---------- VANCOUVER ----------
Gola, G., Gallo-Rodriguez, C. Synthesis of α-d-Glcp-(1→3)-α-d-Galf-(1→2)-α-l- Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis α-d-galactofuranosylation. RSC Adv. 2014;4(7):3368-3382.
http://dx.doi.org/10.1039/c3ra45658g