Synthesis of 6-deoxy-5-thio-D-glucose.
Identifieur interne : 002762 ( PubMed/Corpus ); précédent : 002761; suivant : 002763Synthesis of 6-deoxy-5-thio-D-glucose.
Auteurs : E. Boz ; S. Boros ; J. Kuszmann ; E. Gács-BaitzSource :
- Carbohydrate research [ 0008-6215 ] ; 1996.
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
Links to Exploration step
pubmed:8823905Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis of 6-deoxy-5-thio-D-glucose.</title>
<author><name sortKey="Boz, E" sort="Boz, E" uniqKey="Boz E" first="E" last="Boz">E. Boz</name>
<affiliation><nlm:affiliation>Institute for Drug Research, Budapest, Hungary.</nlm:affiliation>
</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>
</titleStmt>
<publicationStmt><idno type="wicri:source">PubMed</idno>
<date when="1996">1996</date>
<idno type="RBID">pubmed:8823905</idno>
<idno type="pmid">8823905</idno>
<idno type="doi">10.1016/0008-6215(96)00143-7</idno>
<idno type="wicri:Area/PubMed/Corpus">002762</idno>
<idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">002762</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title xml:lang="en">Synthesis of 6-deoxy-5-thio-D-glucose.</title>
<author><name sortKey="Boz, E" sort="Boz, E" uniqKey="Boz E" first="E" last="Boz">E. Boz</name>
<affiliation><nlm:affiliation>Institute for Drug Research, Budapest, Hungary.</nlm:affiliation>
</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="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" xml:lang="en"><term>Magnetic Resonance Spectroscopy</term>
<term>Molecular Conformation</term>
<term>Molecular Structure</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>
<pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">8823905</PMID>
<DateCompleted><Year>1997</Year>
<Month>03</Month>
<Day>10</Day>
</DateCompleted>
<DateRevised><Year>2019</Year>
<Month>08</Month>
<Day>13</Day>
</DateRevised>
<Article PubModel="Print"><Journal><ISSN IssnType="Print">0008-6215</ISSN>
<JournalIssue CitedMedium="Print"><Volume>290</Volume>
<Issue>2</Issue>
<PubDate><Year>1996</Year>
<Month>Sep</Month>
<Day>02</Day>
</PubDate>
</JournalIssue>
<Title>Carbohydrate research</Title>
<ISOAbbreviation>Carbohydr. Res.</ISOAbbreviation>
</Journal>
<ArticleTitle>Synthesis of 6-deoxy-5-thio-D-glucose.</ArticleTitle>
<Pagination><MedlinePgn>159-73</MedlinePgn>
</Pagination>
<Abstract><AbstractText>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.</AbstractText>
</Abstract>
<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Bozó</LastName>
<ForeName>E</ForeName>
<Initials>E</Initials>
<AffiliationInfo><Affiliation>Institute for Drug Research, Budapest, Hungary.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Boros</LastName>
<ForeName>S</ForeName>
<Initials>S</Initials>
</Author>
<Author ValidYN="Y"><LastName>Kuszmann</LastName>
<ForeName>J</ForeName>
<Initials>J</Initials>
</Author>
<Author ValidYN="Y"><LastName>Gács-Baitz</LastName>
<ForeName>E</ForeName>
<Initials>E</Initials>
</Author>
</AuthorList>
<Language>eng</Language>
<PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType>
</PublicationTypeList>
</Article>
<MedlineJournalInfo><Country>Netherlands</Country>
<MedlineTA>Carbohydr Res</MedlineTA>
<NlmUniqueID>0043535</NlmUniqueID>
<ISSNLinking>0008-6215</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList><Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D017607">Aluminum Compounds</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D001894">Borohydrides</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D004220">Disulfides</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D018020">Lithium Compounds</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D008698">Mesylates</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D013438">Sulfhydryl Compounds</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D013863">Thioglucosides</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>77UJC875H4</RegistryNumber>
<NameOfSubstance UI="C042073">lithium aluminum hydride</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>87L0B9CPPA</RegistryNumber>
<NameOfSubstance UI="C025364">sodium borohydride</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>9G2MP84A8W</RegistryNumber>
<NameOfSubstance UI="D003847">Deoxyglucose</NameOfSubstance>
</Chemical>
</ChemicalList>
<CitationSubset>IM</CitationSubset>
<MeshHeadingList><MeshHeading><DescriptorName UI="D017607" MajorTopicYN="N">Aluminum Compounds</DescriptorName>
<QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D001894" MajorTopicYN="N">Borohydrides</DescriptorName>
<QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D003847" MajorTopicYN="N">Deoxyglucose</DescriptorName>
<QualifierName UI="Q000031" MajorTopicYN="Y">analogs & derivatives</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D004220" MajorTopicYN="N">Disulfides</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D018020" MajorTopicYN="N">Lithium Compounds</DescriptorName>
<QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D009682" MajorTopicYN="N">Magnetic Resonance Spectroscopy</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D008698" MajorTopicYN="N">Mesylates</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D008968" MajorTopicYN="N">Molecular Conformation</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D013438" MajorTopicYN="N">Sulfhydryl Compounds</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D013863" MajorTopicYN="N">Thioglucosides</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName>
</MeshHeading>
</MeshHeadingList>
</MedlineCitation>
<PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>1996</Year>
<Month>9</Month>
<Day>2</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="medline"><Year>1996</Year>
<Month>9</Month>
<Day>2</Day>
<Hour>0</Hour>
<Minute>1</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez"><Year>1996</Year>
<Month>9</Month>
<Day>2</Day>
<Hour>0</Hour>
<Minute>0</Minute>
</PubMedPubDate>
</History>
<PublicationStatus>ppublish</PublicationStatus>
<ArticleIdList><ArticleId IdType="pubmed">8823905</ArticleId>
<ArticleId IdType="pii">0008621596001437</ArticleId>
<ArticleId IdType="doi">10.1016/0008-6215(96)00143-7</ArticleId>
</ArticleIdList>
</PubmedData>
</pubmed>
</record>
Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Sante/explor/MersV1/Data/PubMed/Corpus
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 002762 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/PubMed/Corpus/biblio.hfd -nk 002762 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien |wiki= Sante |area= MersV1 |flux= PubMed |étape= Corpus |type= RBID |clé= pubmed:8823905 |texte= Synthesis of 6-deoxy-5-thio-D-glucose. }}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/PubMed/Corpus/RBID.i -Sk "pubmed:8823905" \ | HfdSelect -Kh $EXPLOR_AREA/Data/PubMed/Corpus/biblio.hfd \ | NlmPubMed2Wicri -a MersV1
This area was generated with Dilib version V0.6.33. |