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

Research output: Contribution to journal › Article › peer-review

29 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3933-3942
Number of pages	10
Journal	European Journal of Organic Chemistry
Issue number	23
DOIs	https://doi.org/10.1002/ejoc.200800318
Publication status	Published - Aug 2008
Externally published	Yes

Keywords

Furanoid glycals
Glycosyl sulfoxides
Organolithium reagents
Pyranoid glycals
Sulfoxide ligand exchange

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10.1002/ejoc.200800318

Cite this

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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",

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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

Abstract

Keywords

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