The Journal of Organic Chemistry

Chiral aldehydes by ring contraction of pento-and hexopyranoside epoxides

N Rehnberg, G Magnusson

Index: Rehnberg, Nicola; Magnusson, Goeran Journal of Organic Chemistry, 1990 , vol. 55, # 20 p. 5467 - 5476

Full Text: HTML

Citation Number: 25

Abstract

The chiral aldehydes (-)-(2S, 5S)-and (-)-(2S, 5R)-2-[[[dimethyl (1, 1, 2-trimethylpropyl) silyl] oxy] methyl]-5-methoxy-2, 5-dihydrofuran-3-carbaldehyde (2 and 4) were synthesized in 60 and 15% yield, respectively, by lithium bromide induced rearrangement of 6-0-silylated methyl 2, 3-and 3, 4-anhydro-a-and-PD-hexopyranosides, obtained in two steps from methyl a-and P-Dglucopyranoside. Rearrangement of various other pento-and hexoside ...

~99%

α: β Selectivity in the synthesis of 3-substituted, 4-methyl...

[Ganguli, Anjali R.S.; Coward, James K. Tetrahedron Asymmetry, 2005 , vol. 16, # 2 p. 411 - 424]

Lithium cuprate coupling reactions: evaluation of computatio...

[Krohn, Karsten; Gehle, Dietmar; Floerke, Ulrich European Journal of Organic Chemistry, 2005 , # 21 p. 4557 - 4562]

Preparation of 1, 6: 3, 4-dianhydro-β-D-altropyranose as sta...

[Dolezalova, Jitka; Trnka, Tomas; Cerny, Miloslav Collection of Czechoslovak Chemical Communications, 1982 , vol. 47, # 9 p. 2415 - 2422]

High-pressure fast-pyrolysis, fast-hydropyrolysis and cataly...

[Venkatakrishnan, Vinod Kumar; Degenstein, John C.; Smeltz, Andrew D.; Delgass, W. Nicholas; Agrawal, Rakesh; Ribeiro, Fabio H. Green Chemistry, 2014 , vol. 16, # 2 p. 792 - 802]