18524-41-9Relevant academic research and scientific papers
TPAP-catalyzed direct oxidation of primary alcohols to carboxylic acids through stabilized aldehyde hydrates
Schmidt, Andrea-Katharina C.,Stark, Christian B. W.
supporting information; experimental part, p. 4164 - 4167 (2011/10/08)
We present a simple, mild, and highly effective method for the direct conversion of primary alcohols to carboxylic acids. TPAP serves as the catalyst, and NMO?H2O plays a dual role, acting as the co-oxidant and as a reagent for aldehyde hydrate stabilization. This previously unknown stabilizing effect of geminal diols by N-oxides is the key for the efficiency of the overall transformation.
6-S-Phenyl-glycopyranosides as ready precursors to the synthesis of glycuronides
Yu, Biao,Zhu, Xiangming,Hui, Yongzheng
, p. 9403 - 9413 (2007/10/03)
6-S-Phenyl-gluco/galactopyranosides, readily prepared from the corresponding 6-hydroxy-glycosides, were demonstrated to be effective glycosyl donors or acceptors. The resulting coupling products were then easily converted into the corresponding glycuronide-containing compounds under mild conditions.
Application of stabilized sugar-derived phosphoranes in the synthesis of higher carbon monosaccharides. First synthesis of a C21-dialdose
Jarosz, Slawomir,Salanski, Piotr,Mach, Mateusz
, p. 2583 - 2594 (2007/10/03)
C21 Monosaccharide precursors 11 and 12 were synthesized by a coupling of a C12 aldehyde 1 with C9 stabilized phosphoranes 2 and 3 respectively. The 'smaller' C19 sugar 13 was prepared from a C12 alde
Stereoselective ring-opening of acetylated pyranose-1,2-(ethyl orthoacetates)
Saito,Sumita,Ichinose,Kanda
, p. 90 - 96 (2007/10/02)
When acetylated pyranose-1,2-(ethyl orthoacetates) were hydrolyzed in acidic solvents, the ring-opening of the orthoacetate rings was influenced by the axial or equatorial OAc group at C-4 on the pyranoses; on acid-catalyzed hydrolysis, 3,4,6-tri-O-acetyl-α-D-galactopyranose- (8) and methyl 3,4-di-O-acetyl-α-D-galacturonatopyranose-1,2-(ethyl orthoacetate) (16) having an axial OAc group at C-4 on the pyranose rings gave 1,3,4,6-tetra-O-acetyl-α-D-galactopyranose (9) and methyl 1,3,4-tri-O-acetyl-α-D-galacturonatopyranose (23), respectively, whereas 3,4,6-tri-O-acetyl-α-D-glucopyranose- (10) and methyl 3,4-di-O-acetyl-α-D-glucuronatopyranose-1,2-(ethyl orthoacetate) (22) having an equatorial OAc group at C-4 on the pyranose rings gave 2,3,4,6-tetra-O-acetyl-D-glucopyranose (11) and methyl 2,3,4-tri-O-acetyl-D-glucuronatopyranose (24), respectively. On the acid-catalyzed hydrolysis, 3,4-di-O-acetylβ-L-arabinopyranose-1,2-(ethyl orthoacetate) (34) having an axial OAc group at C-4 on the pyranose ring gave a mixture of 1,3,4-tri-O-acetyl-β-L- (35) and 2,3,4-tri-O-acetyl-L-arabinopyranose (36). These selectivities of ring-opening of the 1,2-(orthoacetates) were considered to have resulted from the differences of the conformers of the 1,2-(orthoacids) intermediates derived from the 1,2-(orthoacetates) and the orientation of the acetyl groups at C-4 on the pyranose rings.
Galacturonic Acid Derivatives. I. Galacturonates from Acetyl- and Isopropylidene-D-galactopyranoses
Vogel, Chr.,Boye, H.,Kristen, H.
, p. 28 - 36 (2007/10/02)
Galacturonic acid derivatives to be employed as glycosyl donors in saccharide synthesis are prepared from galacturonic acid itself or from galactose.Various syntheses of 1,2,3,4-tetra-O-acetyl-D-galactopyranuronic acids (6) with differently protected carb
Convenient One-Pot Conversion of Alcohols into Esters via Hemiacetal Intermediates
Lichtenthaler, Frieder W.,Jarglis, Pan,Lorenz, Klaus
, p. 790 - 792 (2007/10/02)
A simple and efficient one-pot oxidative procedure, adaptable to a large scale, is described for the preparation of methyl esters from either primary alcohols or vic-diols.The aldehyde is generated by Swern or periodate oxidation, followed by bromine oxidation of the methyl hemiacetal formed in aqueous methanolic solution.
