104322-41-0

Upstream product

• 67412-71-9 (-)-benzyl 2,3-anhydro-β-D-ribopyranoside 
• 10323-20-3 D-Arabinose 
• 128843-83-4 Benzyl 2,3-anhydro-α-L-lyxopyranoside 

Downstream Products

• 120040-58-6 Benzo[1,3]dioxol-5-yl-((R)-5-benzyloxy-2,5-dihydro-furan-3-yl)-methanol 
• 498-60-2 furan-3-carboxaldehyde 
• 128843-77-6 (2R,4R/S)-2-(Benzyloxy)tetrahydrofuran-4-carbaldehyde 
• 123195-52-8 (-)-(2R,3R)-2-(Benzyloxy)-3-<3,4-(methylenedioxy)benzyl>-4-<<(tert.-butyldimethylsilyl)oxy>methylene>tetrahydrofuran 
• 104873-10-1 (-)-(1S,2S,5R,6S,7R)-2-Formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.0^2,6>dec-8-ene 
• 104873-09-8 (-)-(1S,2R,5R,6R,7R)-2-Formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.0^2,6>dec-8-ene 
• 104816-20-8 (-)-(1R,2R,5R,6R,7S)-2-Formyl-5-(benzyloxy)-4-oxatricyclo<5.2.1.0^2,6>dec-8-ene 
• 123284-70-8 (-)-(2R,3R)-2-benzyloxy-4-<(tert-butyldimethylsilyloxy)methylene>-3-methyltetrahydrofuran 
• 123195-58-4 ((R)-5-Benzyloxy-2,5-dihydro-furan-3-yl)-(4-fluoro-phenyl)-methanol 
• 77232-48-5 5-methyl-2-(phenyl)pyrimidine 
• 113466-37-8 C₁₉H₃₀O₃Si 
• 120040-66-6 (-)-(2S,3R,4R)-2-(Benzyloxy)-4-<3,4-(methylenedioxy)benzoyl>-3-<3,4-(methylenedioxy)benzyl>tetrahydrofuran 
• 120040-64-4 (+)-(2S,3S,4R)-2-(Benzyloxy)-4-<3,4-(methylenedioxy)benzoyl>-3-<<3,4-(methylenedioxy)phenyl>bis(phenylthio)methyl>tetrahydrofuran 
• 120040-62-2 (+)-(2S,3S,4R)-2-(Benzyloxy)-3-<(3,4,5-trimethoxyphenyl)bis(phenylthio)methyl>-4-<3,4-(methylendioxy)benzoyl>tetrahydrofuran 

Relevant academic research and scientific papers

Chiral Aldehydes by Ring Contraction of Pento- and Hexopyranoside Epoxides

The chiral aldehydes (-)-(2S,5S)- and (-)-(2S,5R)-2-oxy>methyl>-5-methoxy-2,5-dihydrofuran-3-carbaldehyde (2 and 4) were synthesized in 60 and 15percent yield, respectively, by lithium bromide induced rearrangement of 6-O-silylated methyl 2,3- and 3,4-anhydro-α- and -β-D-hexopyranosides, obtained in two steps from methyl α- and β-D-glucopyranoside.Rearrangement of various other pento- and hexoside epoxides permitted the suggestion of probable reaction routes.Hydrogenation of the unsaturated aldehydes gave the corresponding saturated aldehydes in good yield.

Chiral Multifunctional Isoprene Units by Ring-Contraction of Riboside Oxiranes

Lithium bromide induced ring-contraction of benzyl 2,3- and 3,4-anhydro-β-D(and L)-ribopyranoside (1 and 4) in HMPA/toluene or tetramethylurea (TMU)/toluene gave (R)(and S)-2-(benzyloxy)-2,5-dihydrofufan-4-carboxaldehyde (2 and 5) together with a small amount of benzyl 4-bromo-4-deoxy-β-L(and D)-lyxopyranoside (3 and 6).The latter compound was formed with lithium bromide in 1,1,1-trichloroethane.Benzyl 2,3- and 3,4-anhydro-2-deuterio-β-L-ribopyranoside (4d and 8d) gave the deuterated aldehyde 5d, which carried a vinylic deuterium atom, wheraes benzyl 2,3-anhydro-4-deuterio-β-L-ribopyranoside (4d' ) gave the nondeuterated aldehyde 5.On the basis of these experiments, the mechanism of the ring-contraction as postulated.

ASYMMETRIC DIELS-ALDER REACTION BETWEEN THE CHIRAL ISOPRENE UNITS 2-(R)-AND (S)-BENZYLOXY-2,5-DIHYDRO-4-FURANCARBOXALDEHYDE AND CYCLOPENTADIENE

The title Diels-Alder reaction gave a mixture of enantiomerically pure adducts with complete norbornane-type monoterpene skeletons.The exo/endo ratio of the products changed from approximately 4:1 at 5 deg to 2:1 at 165 deg.