Ändra sökning
RefereraExporteraLänk till posten
Permanent länk

Direktlänk
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annat format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annat språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf
Reagent-dependent regioselective control in multiple carbohydrate esterifications
KTH, Skolan för kemivetenskap (CHE), Kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi.ORCID-id: 0000-0002-1533-6514
2007 (Engelska)Ingår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 72, nr 4, s. 1499-1502Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

Regioselective control in organotin-mediated multiple acylation of carbohydrates is presented. The acylation reagent could be efficiently used to direct the product formation. Reagent-dependent thermodynamic and kinetic control and dynamic assistance mechanisms are suggested, resulting in the efficient preparation of building blocks that normally require many steps with traditional synthesis.

Ort, förlag, år, upplaga, sidor
2007. Vol. 72, nr 4, s. 1499-1502
Nyckelord [en]
D-GLUCOPYRANOSIDE; HYDROXYL GROUP; BENZOYLATION; OLIGOSACCHARIDES; DERIVATIVES; SELECTIVITY; ALKYLATION; ACTIVATION; ACYLATION; SUGARS
Nationell ämneskategori
Organisk kemi
Identifikatorer
URN: urn:nbn:se:kth:diva-6397DOI: 10.1021/jo0620821ISI: 000244071100062Scopus ID: 2-s2.0-33846986010OAI: oai:DiVA.org:kth-6397DiVA, id: diva2:139839
Anmärkning
QC 20100709Tillgänglig från: 2006-11-22 Skapad: 2006-11-22 Senast uppdaterad: 2019-12-20Bibliografiskt granskad
Ingår i avhandling
1. Efficient Carbohydrate Synthesis By Intra- and Supramolecular Control
Öppna denna publikation i ny flik eller fönster >>Efficient Carbohydrate Synthesis By Intra- and Supramolecular Control
2009 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

The Lattrell-Dax method of nitrite-mediated substitution of carbohydrate triflates is an efficient method to generate structures of inverse configuration. In this study, the effects of the neighboring group on the Lattrell-Dax inversion were explored. A new carbohydrate/anion host-guest system was discovered and the ambident reactivity of the nitrite anion was found to cause a complicated behavior of the reaction. It has been demonstrated that a neighboring equatorial ester group plays a highly important role in this carbohydrate epimerization reaction, restricting the nitrite N-attack, thus resulting in O-attack only and inducing the formation of inversion compounds in good yields. Based on this effect, efficient synthetic routes to a range of carbohydrate structures, notably β-D-mannosides and β-D-talosides, were designed by use of double parallel and double serial inversion. A supramolecularly activated, triggered cascade reaction was also developed. This cascade reaction is triggered by a deprotonation process that is activated by anions. It was found that the anions can activate this reaction following their hydrogen bonding tendencies to the hydroxyl group in aprotic solvents.

Ort, förlag, år, upplaga, sidor
Stockholm: KTH, 2009. s. 59
Serie
Trita-CHE-Report, ISSN 1654-1081 ; 2009:2
Nyckelord
Carbohydrate Chemistry, Supramolecular Control, Ambident Reactivity
Nationell ämneskategori
Organisk kemi
Identifikatorer
urn:nbn:se:kth:diva-9882 (URN)978-91-7415-207-4 (ISBN)
Disputation
2009-02-05, F3, KTH, Lindstedtsvägen 26, Stockholm, 10:00 (Engelska)
Opponent
Handledare
Anmärkning
QC 20100709Tillgänglig från: 2009-01-27 Skapad: 2009-01-26 Senast uppdaterad: 2019-12-20Bibliografiskt granskad
2. Efficient carbohydrate synthesis by controlled inversion strategies
Öppna denna publikation i ny flik eller fönster >>Efficient carbohydrate synthesis by controlled inversion strategies
2006 (Engelska)Licentiatavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

The Lattrell-Dax method of nitrite-mediated substitution of carbohydrate triflates is an efficient method to generate structures of inverse configuration. In this study it has been demonstrated that a neighboring equatorial ester group plays a highly important role in this carbohydrate epimerization reaction, inducing the formation of inversion compounds in good yields. Based on this effect, efficient synthetic routes to a range of carbohydrate structures, notably β-D-mannosides and β-D-talosides, were designed. By use of the ester activation effect for neighboring groups, a double parallel as well as a double serial inversion strategy was developed.

Ort, förlag, år, upplaga, sidor
Stockholm: KTH, 2006. s. 40
Serie
Trita-IOK, ISSN 1100-7974 ; 107
Nyckelord
Carbohydrate Chemistry, Carbohydrate Protection, Epimerization, Inversion, Dynamic, Regioselective Control, Neighboring Group Participation
Nationell ämneskategori
Organisk kemi
Identifikatorer
urn:nbn:se:kth:diva-4179 (URN)91-7178-502-7 (ISBN)
Presentation
2006-11-30, E2, KTH, Lindstedtsvägen 3, Stockholm, 10:00
Handledare
Anmärkning
QC 20101111Tillgänglig från: 2006-11-22 Skapad: 2006-11-22 Senast uppdaterad: 2010-11-11Bibliografiskt granskad

Open Access i DiVA

Fulltext saknas i DiVA

Övriga länkar

Förlagets fulltextScopushttp://pubs.acs.org/doi/abs/10.1021/jo0620821

Sök vidare i DiVA

Av författaren/redaktören
Dong, HaiPei, ZhichaoByström, StyrbjörnRamström, Olof
Av organisationen
Kemi
I samma tidskrift
Journal of Organic Chemistry
Organisk kemi

Sök vidare utanför DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetricpoäng

doi
urn-nbn
Totalt: 131 träffar
RefereraExporteraLänk till posten
Permanent länk

Direktlänk
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annat format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annat språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf