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

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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.

I: European Journal of Organic Chemistry, Bind 2014, Nr. 35, 2014, s. 7924-7939.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Frihed, T, Pedersen, CM & Bols, M 2014, 'Synthesis of all eight stereoisomeric 6-deoxy-l-hexopyranosyl donors - trends in using stereoselective reductions or mitsunobu epimerizations', European Journal of Organic Chemistry, bind 2014, nr. 35, s. 7924-7939. https://doi.org/10.1002/ejoc.201403074

APA

Frihed, T., Pedersen, C. M., & Bols, M. (2014). Synthesis of all eight stereoisomeric 6-deoxy-l-hexopyranosyl donors - trends in using stereoselective reductions or mitsunobu epimerizations. European Journal of Organic Chemistry, 2014(35), 7924-7939. https://doi.org/10.1002/ejoc.201403074

Vancouver

Frihed T, Pedersen CM, Bols M. Synthesis of all eight stereoisomeric 6-deoxy-l-hexopyranosyl donors - trends in using stereoselective reductions or mitsunobu epimerizations. European Journal of Organic Chemistry. 2014;2014(35):7924-7939. https://doi.org/10.1002/ejoc.201403074

Author

Frihed, Tobias ; Pedersen, Christian Marcus ; Bols, Mikael. / Synthesis of all eight stereoisomeric 6-deoxy-l-hexopyranosyl donors - trends in using stereoselective reductions or mitsunobu epimerizations. I: European Journal of Organic Chemistry. 2014 ; Bind 2014, Nr. 35. s. 7924-7939.

Bibtex

@article{c7bbb0d162b64c858b0cc03a1d0c29c6,
title = "Synthesis of all eight stereoisomeric 6-deoxy-l-hexopyranosyl donors - trends in using stereoselective reductions or mitsunobu epimerizations",
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",
author = "Tobias Frihed and Pedersen, {Christian Marcus} and Mikael Bols",
year = "2014",
doi = "10.1002/ejoc.201403074",
language = "English",
volume = "2014",
pages = "7924--7939",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "35",

}

RIS

TY - JOUR

T1 - Synthesis of all eight stereoisomeric 6-deoxy-l-hexopyranosyl donors - trends in using stereoselective reductions or mitsunobu epimerizations

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

VL - 2014

SP - 7924

EP - 7939

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 35

ER -

ID: 131020797