eprintid: 1472231
rev_number: 26
eprint_status: archive
userid: 608
dir: disk0/01/47/22/31
datestamp: 2016-01-19 15:54:56
lastmod: 2021-09-19 23:29:05
status_changed: 2016-01-19 15:54:56
type: article
metadata_visibility: show
creators_name: Foster, RW
creators_name: Tame, CJ
creators_name: Bučar, DK
creators_name: Hailes, HC
creators_name: Sheppard, TD
title: Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses
ispublished: pub
divisions: UCL
divisions: B04
divisions: C06
divisions: F56
keywords: arabinose, biomass, cyclization, hydrazines, tetrahydrofurans
note: © 2015 The Authors. Published by Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim. This is an open access article under the terms of the Creative Commons At-
tributionLicense, whichpermits use, distributionand reproduction in any
medium, provided the original work is properly cited.
abstract: L-Arabinose is an abundant resource available as a waste product of the sugar beet industry. Through use of a hydrazone-based strategy, L-arabinose was selectively dehydrated to form a chiral tetrahydrofuran on a multi-gram scale without the need for protecting groups. This approach was extended to other biomass-derived reducing sugars and the mechanism of the key cyclization investigated. This methodology was applied to the synthesis of a range of functionalized chiral tetrahydrofurans, as well as a formal synthesis of 3R-3-hydroxymuscarine.
date: 2015-11-02
date_type: published
official_url: http://dx.doi.org/10.1002/chem.201503510
oa_status: green
full_text_type: pub
primo: open
primo_central: open_green
article_type_text: Journal Article
verified: verified_manual
elements_id: 1066972
doi: 10.1002/chem.201503510
lyricists_name: Bucar, Dejan-Kresimir
lyricists_name: Hailes, Helen
lyricists_name: Sheppard, Thomas
lyricists_id: DBUCA58
lyricists_id: HCHAI24
lyricists_id: TSHEP42
actors_name: Sheppard, Thomas
actors_id: TSHEP42
actors_role: owner
full_text_status: public
publication: Chemistry
volume: 21
number: 45
pagerange: 15947-15950
event_location: Germany
issn: 1521-3765
citation:        Foster, RW;    Tame, CJ;    Bučar, DK;    Hailes, HC;    Sheppard, TD;      (2015)    Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses.                   Chemistry , 21  (45)   pp. 15947-15950.    10.1002/chem.201503510 <https://doi.org/10.1002/chem.201503510>.       Green open access   
 
document_url: https://discovery.ucl.ac.uk/id/eprint/1472231/1/48%20SugarDehydration.pdf