The allyl ether as a protecting group in carbohydrate chemistry. Part 11. The 3-methylbut-2-enyl (‘prenyl’) group
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 738-740
- https://doi.org/10.1039/p19800000738
Abstract
The ‘prenyl’ group in ally 3,4,6-tri-O-benzyl-2-O-(3-methylbut-2-enyl)-α-D-galactopyranoside was stable to the action of chlorotris(triphenylphosphine)rhodium(I) during 24 h, whilst the allyl group was isomerised within 1 h. Previous work has shown that the but-2-enyl group is completely isomerised within 24 h by the rhodium catalyst. Thus an allyl group can be removed without affecting a ‘prenyl’ group in the same molecule. The ‘prenyl’ group is cleaved at about the same rate as a but-2-enyl group by potassium t-butoxide in dimethyl sulphoxide. The isomerisation of the allyl group by the rhodium catalyst gives a mixture of cis- and trans-prop-1-enyl ethers.This publication has 3 references indexed in Scilit:
- The allyl ether as a protecting group in carbohydrate chemistry. Part 10. Synthesis of 3-O-(β-D-galactopyranosyl 3-sulphate)-2-O-hexadecanoyl-1-O-hexadecyl-L-glycerol, ‘seminolipid’Journal of the Chemical Society, Perkin Transactions 1, 1979
- Synthesis of blood-group substances. Part 7. Synthesis of the branched trisaccharide O-α-L-fucopyranosyl-(1 → 3)-[O-β-D-galactopyranosyl-(1 → 4)]-2-acetamido-2-deoxy-D-glucopyranoseJournal of the Chemical Society, Perkin Transactions 1, 1979
- Synthesis of blood-group substances. Part 8. A synthesis of the branched trisaccharide 2-acetamido-2-deoxy-4-O-(α-L-fucopyranosyl)-3-O-(β-D-galactopyranosyl)-D-glucopyranoseJournal of the Chemical Society, Perkin Transactions 1, 1979