Synthesis of 6-deoxy-5-thio-D-glucose.
Identifieur interne : 002762 ( PubMed/Curation ); précédent : 002761; suivant : 002763Synthesis 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
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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)
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