Syntheses of 6-Deoxyhex-5-enopyranosides from 6-Bromo-6-deoxy- or 6-O-p-Tolylsulfonylhexopyranosides by the Use of DBU in DMSO
Open Access
- 1 April 1993
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 66 (4) , 1156-1165
- https://doi.org/10.1246/bcsj.66.1156
Abstract
Various kinds of nonbranched and methyl-branched 6-deoxyhex-5-enopyranoside derivatives were prepared from 6-bromo-6-deoxy or 6-O-p-tolylsulfonylhexopyranoside in a one-pot procedure by a successive treatment with iodide anion and 1,8-diazabicyclo[5.4.0]undec-7-ene in dimethyl sulfoxide. The scope and limitations of this reaction have become apparent by observing the reactions of 18 substrates. The yields of altropyranoside and 2-deoxyribo-hexopyranoside derivatives were high, except for the 2,3-anhydropyranoside derivative. Methyl-branched 6-deoxyhex-5-enopyranoside derivatives were also obtained in practical yields.This publication has 6 references indexed in Scilit:
- Stereoselectivities in Catalytic Hydrogenation of Several Branched-Chain 6-Deoxyhex-5-enopyranosides.A Synthesis of Branched-Chain Methyl 6-Deoxy-β-l-hexopyranosideBulletin of the Chemical Society of Japan, 1992
- Branched-chain Sugars. XXXVI. A New Synthesis of Methyl 4-O-Benzoyl-3-benzoylamino-2,3,6-trideoxy-3-C-methyl-α-l-xylo-hexopyranoside, a Derivative of the Branched-chain Amino Sugar of Antibiotic A35512BBulletin of the Chemical Society of Japan, 1984
- Synthesis of methyl 2-acetamido-2,3,6-trideoxy-β-l-lyxo-hexopyranosideCarbohydrate Research, 1983
- Preparative syntheses of 2,6-dideoxy-α-L-lyxo-hexose (2-deoxy-α-L-fucose) and its D-ribo epimer (digitoxose)Carbohydrate Research, 1977
- Synthesis of macrolide antibiotics. I. Stereospecific addition of methyllithium and methylmagnesium iodide to methyl .alpha.-D-xylo-hexopyranosid-4-ulose derivatives. Determination of the configuration at the branching carbon atom by carbon-13 nuclear magnetic resonance spectroscopyThe Journal of Organic Chemistry, 1974
- Synthesis of carbohydrate derivatives containing vinylic thioether groups1Carbohydrate Research, 1971