Synthesis of all eight stereoisomeric 6-deoxy-l-hexopyranosyl donors - trends in using stereoselective reductions or mitsunobu epimerizations

Tobias Frihed; Christian Marcus Pedersen; Mikael Bols

doi:10.1002/ejoc.201403074

Synthesis of all eight stereoisomeric 6-deoxy-l-hexopyranosyl donors - trends in using stereoselective reductions or mitsunobu epimerizations

Tobias Frihed, Christian Marcus Pedersen^*, Mikael Bols

^*Corresponding author for this work

Department of Chemistry

21 Citations (Scopus)

Abstract

The synthesis of all eight rare but biologically important 6deoxy-L-hexoses as their thioglycoside glycosyl donors starting from the commercially available L-rhamnose or L-fucose is reported. The synthesis of all eight 6-deoxy-L-hexoses was accomplished using a variety of epimerization methods, which revealed some general trends. The stereoselective reduction of 4-oxopyranosides could be predicted by the Cram chelation model, while Mitsunobu conditions led to elimination in some substrates.

Original language	English
Journal	European Journal of Organic Chemistry
Volume	2014
Issue number	35
Pages (from-to)	7924-7939
Number of pages	16
ISSN	1434-193X
DOIs	https://doi.org/10.1002/ejoc.201403074
Publication status	Published - 2014

Keywords

6-Deoxy-l-sugars
Carbohydrates
Diastereoselectivity
Nucleophilic substitution
Reduction
Substituent effects

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Synthesis of all eight stereoisomeric 6-deoxy-l-hexopyranosyl donors - trends in using stereoselective reductions or mitsunobu epimerizations. / Frihed, Tobias; Pedersen, Christian Marcus ; Bols, Mikael.

In: European Journal of Organic Chemistry, Vol. 2014, No. 35, 2014, p. 7924-7939.

Research output: Contribution to journal › Journal article › Research › peer-review

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abstract = "The synthesis of all eight rare but biologically important 6deoxy-L-hexoses as their thioglycoside glycosyl donors starting from the commercially available L-rhamnose or L-fucose is reported. The synthesis of all eight 6-deoxy-L-hexoses was accomplished using a variety of epimerization methods, which revealed some general trends. The stereoselective reduction of 4-oxopyranosides could be predicted by the Cram chelation model, while Mitsunobu conditions led to elimination in some substrates.",

keywords = "6-Deoxy-l-sugars, Carbohydrates, Diastereoselectivity, Nucleophilic substitution, Reduction, Substituent effects",

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year = "2014",

doi = "10.1002/ejoc.201403074",

language = "English",

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AU - Frihed, Tobias

AU - Pedersen, Christian Marcus

AU - Bols, Mikael

PY - 2014

Y1 - 2014

N2 - The synthesis of all eight rare but biologically important 6deoxy-L-hexoses as their thioglycoside glycosyl donors starting from the commercially available L-rhamnose or L-fucose is reported. The synthesis of all eight 6-deoxy-L-hexoses was accomplished using a variety of epimerization methods, which revealed some general trends. The stereoselective reduction of 4-oxopyranosides could be predicted by the Cram chelation model, while Mitsunobu conditions led to elimination in some substrates.

AB - The synthesis of all eight rare but biologically important 6deoxy-L-hexoses as their thioglycoside glycosyl donors starting from the commercially available L-rhamnose or L-fucose is reported. The synthesis of all eight 6-deoxy-L-hexoses was accomplished using a variety of epimerization methods, which revealed some general trends. The stereoselective reduction of 4-oxopyranosides could be predicted by the Cram chelation model, while Mitsunobu conditions led to elimination in some substrates.

KW - 6-Deoxy-l-sugars

KW - Carbohydrates

KW - Diastereoselectivity

KW - Nucleophilic substitution

KW - Reduction

KW - Substituent effects

U2 - 10.1002/ejoc.201403074

DO - 10.1002/ejoc.201403074

M3 - Journal article

AN - SCOPUS:84919363713

SN - 1434-193X

VL - 2014

SP - 7924

EP - 7939

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 35

ER -

Synthesis of all eight stereoisomeric 6-deoxy-l-hexopyranosyl donors - trends in using stereoselective reductions or mitsunobu epimerizations

Abstract

Keywords

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