Synthesis of 6-deoxy-5-thio-D-glucose.
Identifieur interne : 003E06 ( Main/Exploration ); précédent : 003E05; suivant : 003E07Synthesis of 6-deoxy-5-thio-D-glucose.
Auteurs : E. Boz [Hongrie] ; S. Boros ; J. Kuszmann ; E. Gács-BaitzSource :
- Carbohydrate research [ 0008-6215 ] ; 1996.
Descripteurs français
- KwdFr :
- Composés de l'aluminium (métabolisme), Composés du lithium (métabolisme), Conformation moléculaire, Disulfures (synthèse chimique), Désoxyglucose (analogues et dérivés), Méthanesulfonates (synthèse chimique), Spectroscopie par résonance magnétique, Structure moléculaire, Thioglucosides (synthèse chimique), Thiols (synthèse chimique), Tétrahydroborates (métabolisme).
- MESH :
- analogues et dérivés : Désoxyglucose.
- métabolisme : Composés de l'aluminium, Composés du lithium, Tétrahydroborates.
- synthèse chimique : Disulfures, Méthanesulfonates, Thioglucosides, Thiols.
- Conformation moléculaire, Spectroscopie par résonance magnétique, Structure moléculaire.
English descriptors
- KwdEn :
- Aluminum Compounds (metabolism), Borohydrides (metabolism), Deoxyglucose (analogs & derivatives), Disulfides (chemical synthesis), Lithium Compounds (metabolism), Magnetic Resonance Spectroscopy, Mesylates (chemical synthesis), Molecular Conformation, Molecular Structure, Sulfhydryl Compounds (chemical synthesis), Thioglucosides (chemical synthesis).
- MESH :
- chemical , analogs & derivatives : Deoxyglucose.
- chemical , chemical synthesis : Disulfides, Mesylates, Sulfhydryl Compounds, Thioglucosides.
- chemical , metabolism : Aluminum Compounds, Borohydrides, Lithium Compounds.
- Magnetic Resonance Spectroscopy, Molecular Conformation, Molecular Structure.
Abstract
Three routes were investigated for the conversion of D-glucose into the title compound. In the first approach, reduction of the 5,6-thiirane ring of 5,6-dideoxy-5, 6-epithio-1,2-O-isopropylidene-alpha-D-glucofuranose (17) as well as that of its 3-O-allyl derivative (13) with lithium aluminium hydride was investigated; 17 afforded the corresponding 6-deoxy derivative besides di-, tri-, and poly-mers, whereas only polymers were formed from 13. In the second approach, the oxirane ring of 3-O-allyl-5,6-anhydro-1,2-O-isopropylidene-beta-L-idofuranose was reduced by sodium borohydride and the resulting 6-deoxy derivative was converted into the 5-thiobenzoate; the corresponding hex-4-enofuranose was formed as a byproduct. In the third approach partial mesylation of methyl 5-thio-alpha-D-glucopyranoside was attempted, but the 6-mesylate 27 could be isolated only in modest yield (28%) together with rearranged 2,5-thioanhydromannofuranoside derivatives. The mechanism of this rearrangement is discussed in detail. The 6-mesylate 27 was converted via the 6-iodo derivative into the title compound.
DOI: 10.1016/0008-6215(96)00143-7
PubMed: 8823905
Affiliations:
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Boz</name><affiliation wicri:level="3"><nlm:affiliation>Institute for Drug Research, Budapest, Hungary.</nlm:affiliation><country xml:lang="fr">Hongrie</country><wicri:regionArea>Institute for Drug Research, Budapest</wicri:regionArea><placeName><settlement type="city">Budapest</settlement><region nuts="2">Hongrie centrale</region></placeName></affiliation></author><author><name sortKey="Boros, S" sort="Boros, S" uniqKey="Boros S" first="S" last="Boros">S. Boros</name></author><author><name sortKey="Kuszmann, J" sort="Kuszmann, J" uniqKey="Kuszmann J" first="J" last="Kuszmann">J. Kuszmann</name></author><author><name sortKey="Gacs Baitz, E" sort="Gacs Baitz, E" uniqKey="Gacs Baitz E" first="E" last="Gács-Baitz">E. Gács-Baitz</name></author></analytic><series><title level="j">Carbohydrate research</title><idno type="ISSN">0008-6215</idno><imprint><date when="1996" type="published">1996</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aluminum Compounds (metabolism)</term><term>Borohydrides (metabolism)</term><term>Deoxyglucose (analogs & derivatives)</term><term>Disulfides (chemical synthesis)</term><term>Lithium Compounds (metabolism)</term><term>Magnetic Resonance Spectroscopy</term><term>Mesylates (chemical synthesis)</term><term>Molecular Conformation</term><term>Molecular Structure</term><term>Sulfhydryl Compounds (chemical synthesis)</term><term>Thioglucosides (chemical synthesis)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Composés de l'aluminium (métabolisme)</term><term>Composés du lithium (métabolisme)</term><term>Conformation moléculaire</term><term>Disulfures (synthèse chimique)</term><term>Désoxyglucose (analogues et dérivés)</term><term>Méthanesulfonates (synthèse chimique)</term><term>Spectroscopie par résonance magnétique</term><term>Structure moléculaire</term><term>Thioglucosides (synthèse chimique)</term><term>Thiols (synthèse chimique)</term><term>Tétrahydroborates (métabolisme)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Deoxyglucose</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Disulfides</term><term>Mesylates</term><term>Sulfhydryl Compounds</term><term>Thioglucosides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Aluminum Compounds</term><term>Borohydrides</term><term>Lithium Compounds</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Désoxyglucose</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Composés de l'aluminium</term><term>Composés du lithium</term><term>Tétrahydroborates</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Disulfures</term><term>Méthanesulfonates</term><term>Thioglucosides</term><term>Thiols</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Magnetic Resonance Spectroscopy</term><term>Molecular Conformation</term><term>Molecular Structure</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Conformation moléculaire</term><term>Spectroscopie par résonance magnétique</term><term>Structure moléculaire</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Three routes were investigated for the conversion of D-glucose into the title compound. In the first approach, reduction of the 5,6-thiirane ring of 5,6-dideoxy-5, 6-epithio-1,2-O-isopropylidene-alpha-D-glucofuranose (17) as well as that of its 3-O-allyl derivative (13) with lithium aluminium hydride was investigated; 17 afforded the corresponding 6-deoxy derivative besides di-, tri-, and poly-mers, whereas only polymers were formed from 13. In the second approach, the oxirane ring of 3-O-allyl-5,6-anhydro-1,2-O-isopropylidene-beta-L-idofuranose was reduced by sodium borohydride and the resulting 6-deoxy derivative was converted into the 5-thiobenzoate; the corresponding hex-4-enofuranose was formed as a byproduct. In the third approach partial mesylation of methyl 5-thio-alpha-D-glucopyranoside was attempted, but the 6-mesylate 27 could be isolated only in modest yield (28%) together with rearranged 2,5-thioanhydromannofuranoside derivatives. The mechanism of this rearrangement is discussed in detail. The 6-mesylate 27 was converted via the 6-iodo derivative into the title compound.</div></front></TEI><affiliations><list><country><li>Hongrie</li></country><region><li>Hongrie centrale</li></region><settlement><li>Budapest</li></settlement></list><tree><noCountry><name sortKey="Boros, S" sort="Boros, S" uniqKey="Boros S" first="S" last="Boros">S. Boros</name><name sortKey="Gacs Baitz, E" sort="Gacs Baitz, E" uniqKey="Gacs Baitz E" first="E" last="Gács-Baitz">E. Gács-Baitz</name><name sortKey="Kuszmann, J" sort="Kuszmann, J" uniqKey="Kuszmann J" first="J" last="Kuszmann">J. Kuszmann</name></noCountry><country name="Hongrie"><region name="Hongrie centrale"><name sortKey="Boz, E" sort="Boz, E" uniqKey="Boz E" first="E" last="Boz">E. Boz</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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