7241-20-5Relevant articles and documents
Catalytic Enantioselective α,β,γ-Trioxygenation
Chen, Jason S.,Abeykoon, Gayan A.
, p. 6050 - 6053 (2016/01/09)
Applying a catalytic enantioselective aldehyde α-oxygenation condition to an enal substrate led to the discovery of the first α,β,γ-trifunctionalization cascade of enals. Under optimal conditions, a tryptophan-derived imidazolidinone catalyst in fluorinated aromatic solvents provided α,β,γ-trioxyaldehydes in up to 51% isolated yield (average of 80% yield per oxygenation step) and 85:15 er. Substitution at the δ position was tolerated, but not at the α, β, or γ positions. The reaction proceeded through initial TEMPO incorporation at the γ position, and rapid racemization of this intermediate, reversible conjugate addition of water, followed by TEMPO incorporation at the α position to set all three stereocenters with double dynamic kinetic resolution.
Oxygenated stereotriads with definite absolute configuration by lipase-mediated kinetic resolution: De novo synthesis of imino sugars and 6-deoxy- C-glycosides
Acctti, Daniela,Brenna, Elisabetta,Gatti, Francesco G.
supporting information; experimental part, p. 4468 - 4475 (2010/10/02)
The lipase-mediated kinetic resolution of compound 1 was investigated, to prepare chiral synthons showing oxygenated stereotriads in a definite configurational arrangement. These key intermediates were embedded in biologically relevant structures, such as hydroxylated pyrrolidine 3 and C-phenyl glycosides by classical organic reactions.
Electroorganic synthesis, 62: Anodic heterocoupling (mixed Kolbe electrolysis) of carbohydrate carboxylic acids with alkanoic acids to C-glycosides
Harenbrock, Michael,Matzeit, Agnes,Schaefer, Hans J.
, p. 55 - 62 (2007/10/03)
2-Deoxy carbohydrate carboxylic acids 1-3 were prepared from glucal 4, acetobromoglucose 5, and D-galactose (7), respectively. The acids 1-3 were electrolyzed with different coacids at controlled current in methanol at platinum electrodes in an undivided
Formation of 1-Deoxy-D-threo-pentulose and 1-Deoxy-L-threo-pentulose by Cell-free Extracts of Microorganisms
Yokota, Akira,Sasajima, Ken-ichi
, p. 149 - 158 (2007/10/02)
A new enzymatic acyloin-type condensation between pyruvate (or acetoin or methylacetoin) and D-glyceraldehyde was found to be catalyzed by cell-free extracts of a transketolase mutant of Bacillus pumilus IFO 12089.The reaction product (1) was isolated and determined to be 1-deoxy-D-threo-pentulose (D-DTP), which is considered to be a precursor of the five-carbon unit of the thiazole ring thiamine. 1-Deoxy-L-threo-pentulose (L-DTP, 2) was synthesized similarly when L-glyceraldehyde was used instead of D-glyceraldehyde.The configurations of 1 and 2 were confirmed by reduction to the corresponding 1-deoxy-pentitols.Similar enzyme activities were also detected in cell-free extracts of all the wild-type strains tested of bacteria, actinomycetes, yeasts, and molds.These results suggest that the D-DTP synthesizing enzyme plays an important role in the biosynthesis of the thiazole ring of thiamine in vivo.
