liu.seSearch for publications in DiVA
Endre søk
RefereraExporteraLink to record
Permanent link

Direct link
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • oxford
  • Annet format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annet språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf
Synthesis of oligosaccharides designed to form micelles, corresponding to structures found in ovarian cyst fluid
Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden Linkoping Univ, Dept Chem, S-58183 Linkoping, Sweden.
Linköpings universitet, Tekniska högskolan. Linköpings universitet, Institutionen för fysik, kemi och biologi, Organisk Kemi.
2000 (engelsk)Inngår i: Journal of carbohydrate chemistry, ISSN 0732-8303, E-ISSN 1532-2327, Vol. 19, nr 1, s. 25-51Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

The syntheses of alpha-D-GlcpNAc-(1-->4)-beta-D-Galp-(1-->4)-beta-D-GlcNAc-(1-->O)-(CH2)(15)CH3 (1) and fragments thereof, corresponding to structures found in human ovarian cyst fluid, are described. Silver triflate promoted coupling of 3.4,6-tri-O-acetyl-2-azido-2-deoxy-beta-D-glucopyranosyl bromide (12) and galactose acceptor (11) gave a disaccharide donor (13), which was readily transformed into the corresponding bromo-derivative 18. For the synthesis of disaccharide beta-D-Galp-(1-->4)-D-GlcNAc, several differently protected glucosamine accepters were prepared. It was found that cetyl alcohol needed to be introduced after the formation of the P-galactoside bond. Glycosylation of pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-beta-D-glucopyranoside (30) with (3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-glucopyranosyl)-(1-->4)-2,3,6-tri-O-benzoyl-alpha-D-galactopyranosyl bromide (18) by use of silver triflate as promoter gave the desired trisaccharide 31. Finally 31 was transformed via coupling to the long alkyl chain aglycon and deprotection into the title compound 1.

sted, utgiver, år, opplag, sider
2000. Vol. 19, nr 1, s. 25-51
HSV kategori
Identifikatorer
URN: urn:nbn:se:liu:diva-49862OAI: oai:DiVA.org:liu-49862DiVA, id: diva2:270758
Tilgjengelig fra: 2009-10-11 Laget: 2009-10-11 Sist oppdatert: 2017-12-12

Open Access i DiVA

Fulltekst mangler i DiVA

Personposter BETA

Konradsson, Peter

Søk i DiVA

Av forfatter/redaktør
Konradsson, Peter
Av organisasjonen
I samme tidsskrift
Journal of carbohydrate chemistry

Søk utenfor DiVA

GoogleGoogle Scholar

urn-nbn

Altmetric

urn-nbn
Totalt: 133 treff
RefereraExporteraLink to record
Permanent link

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