-
Something wrong with this record ?
An approach to stereoselective preparation of 3-C-glycosylated D- and L-glucals
K. Parkan, L. Werner, Z. Lövyová, E. Prchalová, L. Kniezo
Language English Country Netherlands
Document type Journal Article, Research Support, Non-U.S. Gov't
- MeSH
- Disaccharides chemical synthesis MeSH
- Glycosylation MeSH
- Mandelic Acids chemistry MeSH
- Stereoisomerism MeSH
- Vinyl Compounds chemistry MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
An approach to stereoselective synthesis of alpha- or beta-3-C-glycosylated L- or D-1,2-glucals starting from the corresponding alpha- or beta-glycopyranosylethanals is described. The key step of the approach is the stereoselective cycloaddition of chiral vinyl ethers derived from both enantiomers of mandelic acid. The preparation of 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)methyl]-L-arabino-hex-1-enitol, 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)methyl]-D-arabino-hex-1-enitol, and 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)methyl]-D-arabino-hex-1-enitol serves as an example of this approach.
References provided by Crossref.org
- 000
- 00000naa a2200000 a 4500
- 001
- bmc12025347
- 003
- CZ-PrNML
- 005
- 20130225174543.0
- 007
- ta
- 008
- 120816s2010 ne f 000 0#eng||
- 009
- AR
- 024 7_
- $a 10.1016/j.carres.2009.11.025 $2 doi
- 035 __
- $a (PubMed)20035928
- 040 __
- $a ABA008 $b cze $d ABA008 $e AACR2
- 041 0_
- $a eng
- 044 __
- $a ne
- 100 1_
- $a Parkan, Kamil, $d 1980- $7 xx0124745 $u Department of Chemistry of Natural Compounds, Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic.
- 245 13
- $a An approach to stereoselective preparation of 3-C-glycosylated D- and L-glucals / $c K. Parkan, L. Werner, Z. Lövyová, E. Prchalová, L. Kniezo
- 520 9_
- $a An approach to stereoselective synthesis of alpha- or beta-3-C-glycosylated L- or D-1,2-glucals starting from the corresponding alpha- or beta-glycopyranosylethanals is described. The key step of the approach is the stereoselective cycloaddition of chiral vinyl ethers derived from both enantiomers of mandelic acid. The preparation of 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)methyl]-L-arabino-hex-1-enitol, 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)methyl]-D-arabino-hex-1-enitol, and 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)methyl]-D-arabino-hex-1-enitol serves as an example of this approach.
- 650 _2
- $a disacharidy $x chemická syntéza $7 D004187
- 650 _2
- $a glykosylace $7 D006031
- 650 _2
- $a kyseliny mandlové $x chemie $7 D008333
- 650 _2
- $a stereoizomerie $7 D013237
- 650 _2
- $a vinylové sloučeniny $x chemie $7 D014753
- 655 _2
- $a časopisecké články $7 D016428
- 655 _2
- $a práce podpořená grantem $7 D013485
- 700 1#
- $a Werner, Lukáš. $7 _AN071432
- 700 1#
- $a Lövyová, Zuzana. $7 _AN044741
- 700 1_
- $a Prchalová, Eva
- 700 1_
- $a Kniežo, Ladislav, $d 1944- $7 xx0124743
- 773 0_
- $w MED00001049 $t Carbohydrate research $x 1873-426X $g Roč. 345, č. 3 (2010), s. 352-362
- 856 41
- $u https://pubmed.ncbi.nlm.nih.gov/20035928 $y Pubmed
- 910 __
- $a ABA008 $b sig $c sign $y m
- 990 __
- $a 20120816 $b ABA008
- 991 __
- $a 20130225174752 $b ABA008
- 999 __
- $a ok $b bmc $g 947389 $s 782693
- BAS __
- $a 3
- BAS __
- $a PreBMC
- BMC __
- $a 2010 $b 345 $c 3 $d 352-362 $i 1873-426X $m Carbohydrate research $n Carbohydr Res $x MED00001049
- LZP __
- $a Pubmed-20120816/10/02
