Synthesis of pyranoid and furanoid glycals from glycosyl sulfoxides by treatment with organolithium reagents

Ana M. Gómez; Marta Casillas; Aitor Barrio; Anna Gawel; J. Cristóbal López

doi:10.1002/ejoc.200800318

Synthesis of pyranoid and furanoid glycals from glycosyl sulfoxides by treatment with organolithium reagents

Ana M. Gómez
, Marta Casillas
, Aitor Barrio
, Anna Gawel
, J. Cristóbal López

CSIC - Instituto de Química Orgánica General IQOG

Producción científica: Contribución a una revista › Artículo › revisión exhaustiva

29 Citas (Scopus)

Resumen

Glycosyl sulfoxides can be conveniently transformed into pyranoid or furanoid glycals by treatment with organolithium reagents. The more likely reaction pathway involves a sulfoxide/metal exchange reaction to generate a glycosyllithium derivative that undergoes β-elimination of its C-2 substituent.

Idioma original	Inglés
Páginas (desde-hasta)	3933-3942
Número de páginas	10
Publicación	European Journal of Organic Chemistry
N.º	23
DOI	https://doi.org/10.1002/ejoc.200800318
Estado	Publicada - ago 2008
Publicado de forma externa	Sí

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@article{f0e1e683eb3a42f8a925d6c5ca985e49,

title = "Synthesis of pyranoid and furanoid glycals from glycosyl sulfoxides by treatment with organolithium reagents",

abstract = "Glycosyl sulfoxides can be conveniently transformed into pyranoid or furanoid glycals by treatment with organolithium reagents. The more likely reaction pathway involves a sulfoxide/metal exchange reaction to generate a glycosyllithium derivative that undergoes β-elimination of its C-2 substituent.",

keywords = "Furanoid glycals, Glycosyl sulfoxides, Organolithium reagents, Pyranoid glycals, Sulfoxide ligand exchange",

author = "G{\'o}mez, \{Ana M.\} and Marta Casillas and Aitor Barrio and Anna Gawel and L{\'o}pez, \{J. Crist{\'o}bal\}",

year = "2008",

month = aug,

doi = "10.1002/ejoc.200800318",

language = "English",

pages = "3933--3942",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "23",

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TY - JOUR

T1 - Synthesis of pyranoid and furanoid glycals from glycosyl sulfoxides by treatment with organolithium reagents

AU - Gómez, Ana M.

AU - Casillas, Marta

AU - Barrio, Aitor

AU - Gawel, Anna

AU - López, J. Cristóbal

PY - 2008/8

Y1 - 2008/8

N2 - Glycosyl sulfoxides can be conveniently transformed into pyranoid or furanoid glycals by treatment with organolithium reagents. The more likely reaction pathway involves a sulfoxide/metal exchange reaction to generate a glycosyllithium derivative that undergoes β-elimination of its C-2 substituent.

AB - Glycosyl sulfoxides can be conveniently transformed into pyranoid or furanoid glycals by treatment with organolithium reagents. The more likely reaction pathway involves a sulfoxide/metal exchange reaction to generate a glycosyllithium derivative that undergoes β-elimination of its C-2 substituent.

KW - Furanoid glycals

KW - Glycosyl sulfoxides

KW - Organolithium reagents

KW - Pyranoid glycals

KW - Sulfoxide ligand exchange

UR - https://www.scopus.com/pages/publications/53849113695

U2 - 10.1002/ejoc.200800318

DO - 10.1002/ejoc.200800318

M3 - Article

AN - SCOPUS:53849113695

SN - 1434-193X

SP - 3933

EP - 3942

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 23

ER -

Synthesis of pyranoid and furanoid glycals from glycosyl sulfoxides by treatment with organolithium reagents

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