| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347160 | Tetrahedron: Asymmetry | 2009 | 11 Pages |
Two carbon chain extensions using a Wittig reaction on both a 1-deoxy ribulose derivative and a C-2-branched erythrose derivative are reported. Subsequent dihydroxylation resulted in the synthesis of C-3 and C-4 methyl-branched sugar lactones, the useful synthetic building blocks. Control of the stereoselectivity of both the Wittig reaction and the dihydroxylation is investigated, and 3-C-methyl and 4-C-methyl d-altrono-1,4-lactones and d-glucono-1,4-lactone and 4-C-hydroxymethyl-d-altrono-1,4-lactone were synthesised.
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(4S,5R,E)-Methyl 6-hydroxy-4,5-O-isopropylidene-3-methyl-hex-2-enoateC11H18O5Ee = 100%[α]D17=+41.7 (c 1.28, CHCl3)Source of chirality: d-erythronolactone as starting material
(4S,5R,Z)-Methyl 6-hydroxy-4,5-O-isopropylidene-3-methyl-hex-2-enoateC11H18O5Ee = 100%[α]D21=+45.7 (c 0.6, CHCl3)Source of chirality: d-erythronolactone as starting material
Methyl 3,6-anhydro-2-deoxy-4,5-O-isopropylidene-3-C-methyl-d-allonateC11H18O5Ee = 100%[α]D15=-17.8 (c 1.13, CHCl3)Source of chirality: d-erythronolactone as starting material
Methyl 4,5-O-isopropylidene-3-C-methyl-d-altronoateC11H20O7Ee = 100%[α]D17=+17.8 (c 1.65, acetone)Source of chirality: d-erythronolactone as starting material
Methyl 4,5-O-isopropylidene-3-C-methyl-d-gluconateC11H20O7Ee = 100%[α]D18=+19.6 (c 0.55, acetone)Source of chirality: d-erythronolactone as starting material
5,6-O-Isopropylidene-3-C-methyl-d-altrono-1,4-lactoneC10H16O6Ee = 100%[α]D19=+50.4 (c 0.46, acetone)Source of chirality: d-erythronolactone as starting material
5,6-O-Isopropylidene-3-C-methyl-d-glucono-1,4-lactoneC10H16O6Ee = 100%[α]D21=+74.7 (c 0.25, acetone)Source of chirality: d-erythronolactone as starting material
3-C-Methyl-d-altrono-1,4-lactoneC7H12O6Ee = 100%[α]D22=+63.3 (c 0.15, MeOH)Source of chirality: d-erythronolactone as starting material
3-C-Methyl-d-glucono-1,4-lactoneC7H12O6Ee = 100%[α]D20=+47.1 (c 0.48, H2O)Source of chirality: d-erythronolactone as starting material
2-C-Hydroxymethyl-2,3-O-isopropylidene-d-erythrofuranoseC8H14O5Ee = 100%[α]D20=-51.3 (c 0.91, CHCl3)Source of chirality: d-erythronolactone as starting material
3,6-Anhydro-2-deoxy-4-C-hydroxymethyl-4,5-O-isopropylidene-d-ribo-hexono-1,4-lactoneC10H14O5Ee = 100%[α]D20=-78.3 (c 0.98, CH3CN)Source of chirality: d-erythronolactone as starting material
2-C-Hydroxymethyl-2,3-O-isopropylidene-2-O-tert-butyldiphenylsilyl-d-erythrofuranoseC24H32O5SiEe = 100%[α]D20=-3.5 (c 0.82, CH3CN)Source of chirality: d-erythronolactone as starting material
(4R,5R,E)-Methyl 6-hydroxy-4-C-hydroxymethyl-4,5-O-isopropylidene-4-O-tertbutyldiphenylsilyl-hex-2-enoateC27H36O6SiEe = 100%[α]D20=+1.9 (c 1.275, CH3CN)Source of chirality: d-erythronolactone as starting material
Methyl 3,6-anhydro-2-deoxy-4-C-hydroxymethyl-4,5-O-isopropylidene-4-O-tertbutyldiphenylsilyl-d-gluconateC27H36O6SiEe = 100%[α]D20=-9.8 (c 1.22, CHCl3)Source of chirality: d-erythronolactone as starting material
2-C-Hydroxymethyl-2,3-O-isopropylidene-d-erythrono-1,4-lactoneC8H12O5Ee = 100%[α]D22=-103.4 (c 1.26, CHCl3)Source of chirality: d-erythronolactone as starting material
2-C-Hydroxymethyl-2,3-O-isopropylidene-2-O-trifluoromethanesulfonyl-d-erythrono-1,4-lactoneC9H11F3O7SEe = 100%[α]D17=-52.7 (c 0.7, CHCl3)Source of chirality: d-erythronolactone as starting material
2-C-Iodomethyl-2,3-O-isopropylidene-d-erythrono-1,4-lactoneC8H11IO4Ee = 100%[α]D22=-72.1 (c 0.89, CHCl3)Source of chirality: d-erythronolactone as starting material
2,3-O-Isopropylidene-2-C-methyl-d-erythrono-1,4-lactoneC8H12O4Ee = 100%[α]D20=-95.5 (c 0.69, CHCl3)Source of chirality: d-erythronolactone as starting material
2,3-O-Isopropylidene-2-C-methyl-d-erythronofuranoseC8H14O4Ee = 100%[α]D21=-56.8 (c 1.01, CHCl3)Source of chirality: d-erythronolactone as starting material
Methyl 4-C-hydroxymethyl-4,5-O-isopropylidene-4-O-tert-butyldiphenylsilyl-d-altronateC27H38O8SiEe = 100%[α]D20=+4.8 (c 1.24, CH3CN)Source of chirality: d-erythronolactone as starting material
Methyl 4-C-hydroxymethyl-4,5-O-isopropylidene-4-O-tert-butyldiphenylsilyl-d-gluconateC27H38O8SiEe = 100%[α]D20=-15.5 (c 1.255, CH3CN)Source of chirality: d-erythronolactone as starting material
4-C-Hydroxymethyl-d-altrono-1,4-lactoneC7H12O7Ee = 100%[α]D20=-11.4 (c 1.13, MeOH)Source of chirality: d-erythronolactone as starting material
4-C-Hydroxymethyl-4-O-tert-butyldiphenylsilyl-d-altrono-1,4-lactoneC23H30O7SiEe = 100%[α]D20=-9.8 (c 0.97, CH3CN)Source of chirality: d-erythronolactone as starting material
Methyl 4-C-methyl-4,5-O-isopropylidene-d-altronateC11H20O7Ee = 100%[α]D25=-4.5 (c 0.605, CHCl3)Source of chirality: d-erythronolactone as starting material
Methyl 4-C-methyl-4,5-O-isopropylidene-d-gluconateC11H20O7Ee = 100%[α]D25=-16.3 (c 0.3, CHCl3)Source of chirality: d-erythronolactone as starting material
4-C-Methyl-d-altrono-1,4-lactoneC7H12O6Ee = 100%[α]D25=-2.8 (c 1.09, MeOH)Source of chirality: d-erythronolactone as starting material
4-C-Methyl-d-glucono-1,4-lactoneC7H12O6Ee = 100%[α]D25=+22.2 (c 0.34, MeOH)Source of chirality: d-erythronolactone as starting material
