126-14-7Relevant academic research and scientific papers
A phenylpropanoid glycoside from Vaccaria segetalis
Sang, Shengmin,Lao, Aina,Wang, Hongcheng,Chen, Zhongliang,Uzawa, Jun,Fujimoto, Yasuo
, p. 569 - 571 (1998)
A new phenylpropanoid glycoside, named segetoside A, and a known compound, allantoin, have been isolated from the seeds of Vaccaria segetalis. On the basis of chemical and spectral data, the structure of segetoside A has been established as α-D-(6-O-dihydroferuloyl)glucopyranosyl(1 → 2)-β-D- fructofuranoside.
Isolation and synthesis of trans- and cis-(-)-clovamides and their deoxy analogues from the bark of Dalbergia melanoxylon
R. Van Heerden, Fanie,Vincent Brandt,G. Roux, David
, p. 2125 - 2129 (1980)
N-(3′,4′-Dihydroxy-trans-cinnamoyl)-3-(3,4-dihydroxyphenyl)-L-alanine [(-)-clovamide], the major phenolic metabolite (0.1%) in the bark of Dalbergia melanoxylon, is associated with minor proportions of its cis-isomer, and similar pairs of geometrical isomers of their deoxy analogues N-(4′-hydroxycinnamoyl)-3-(3,4-dihydroxyphenyl)-L-alanine and N-(4′-hydroxycinnamoyl)-3-(4-hydroxyphenyl)-L-alanine. (-)-Trans-clovamide is synthesized by direct condensation of the acid chloride of caffeic acid with L-DOPA. Diagnostic CD spectra of these compounds and 13C spectra of (-)-trans- and (-)-cis-clovamides are recorded.
Rapid, clean, and mild O-acetylation of alcohols and carbohydrates in an ionic liquid
Forsyth, Stewart A.,MacFarlane, Douglas R.,Thomson, Robin J.,Von Itzstein, Mark
, p. 714 - 715 (2002)
Archetypal O-acetylation reactions of alcohols and carbohydrates proceed rapidly in high yield under mild conditions in a dicyanamide based ionic liquid, that is not only an effective solvent but also an active base catalyst.
Tandem acetalation-acetylation of sugars and related derivatives with enolacetates under solvent-free conditions
Mukherjee, Debaraj,Shah, Bhahwal Ali,Gupta, Pankaj,Taneja, Subhash Chandra
, p. 8965 - 8968 (2007)
(Chemical Equation Presented) Molecular iodine catalyzes acetalation and acetylation of reducing sugars and sugar glycosides with stoichiometric amounts of enol acetates under solvent-free conditions, thereby facilitating the synthesis of various types of orthogonally protected sugar derivatives in short time and good yields. The outcome of the reaction can be controlled by variation in temperature. Thus at lower temperature, it is possible to obtain the acetonide acetate as a single product whereas peracetate is the major product at higher temperature.
Cu(ClO4)2·6H2O catalyzed solvent free per-O-acetylation and sequential one-pot conversions of sugars to thioglycosides
Chatterjee, Debnath,Paul, Abhijit,Rajkamal,Yadav, Somnath
, p. 29669 - 29674 (2015/05/20)
The solvent free per-O-acetylation of various reducing and non-reducing sugars has been carried out using stoichiometric amounts of acetic anhydride and copper(ii) perchlorate hexahydrate as the catalyst. The reactions with various reducing monosaccharides have also been followed by a one-pot sequential conversion to the corresponding thioglycosides in high yields. This journal is
I2/ionic liquid as a highly efficient catalyst for per-O-acetylation of sugar under microwave irradiation
Xiong, Xingquan,Yi, Chao,Han, Qian,Shi, Lin,Li, Sizhong
, p. 237 - 243 (2015/09/28)
A practical and highly efficient approach was developed to synthesize peracetylated sugar derivatives using a recyclable iodine/PEG400-based ionic liquid catalyst (I2/IL). The peracetylated sugars were readily obtained in a few minutes in excellent yields (90%-99%, 13 examples) on a multi-gram scale (50.0 mmol) by the reaction of sugar and acetic anhydride under microwave irradiation in the absence of a volatile organic solvent. The desired product was easily obtained by simple extraction with toluene from the reaction mixture, and I2/ILs can be readily recovered and reused at least six times without obvious loss in the yield. When the scale of the per-O-acetylation reaction was increased to 50.0 mmol, the desired product was still obtained in 90% yield after five recycles.
H2SO4-SiO2: Highly efficient and reusable catalyst for per-O-acetylation of carbohydrates under solvent-free conditions
Zhang, Jianbo,Zhang, Bo,Zhou, Jiafen,Li, Juan,Shi, Chunjuan,Huang, Ting,Wang, Zhongfu,Tang, Jie
experimental part, p. 165 - 177 (2012/01/19)
Sulfuric acid immobilized on silica gel (H2SO 4-SiO2) was used as an efficient promoter for per-O-acetylation of carbohydrates with acetic anhydride under solvent-free conditions. The substrates include not only monosaccharides and disaccharides, but also glycosides. The catalyst is recyclable and stable at room temperature, and the reaction protocol is simple, is cost-effective, and gives good isolated yield with high purity. The large-scale reactions also proceeded conveniently and in high yields. Taylor & Francis Group, LLC.
Synthesis of (+)-sucrose via β-d-psicofuranosylation
Uenishi, Jun'ichi,Ueda, Atsushi
experimental part, p. 2210 - 2217 (2009/04/04)
Despite the difficulty of direct β-furanosylation with d-fructose, the synthesis of β-d-fructofuranosyl α-d-glucopyranoside, (+)-sucrose 1, has been achieved stepwise, via β-selective d-psicofuranosylation followed by stereo inversion of a hydroxy group at the C-3 position on the furanose ring. d-Psicofuranosyl donor 10 was prepared in eight steps from d-ribose monoacetonide 3 in excellent yield.
Mild and efficient method for the cleavage of benzylidene acetals using HClO4-SiO2 and direct conversion of acetals to acetates
Agnihotri, Geetanjali,Misra, Anup Kumar
, p. 3653 - 3658 (2007/10/03)
HClO4-SiO2 has been used successfully for the deprotection of benzylidene acetals and the direct conversion of benzylidene acetals to the corresponding di-O-acetates. The reactions are very fast and yields are excellent.
HClO4-SiO2 catalyzed per-O-acetylation of carbohydrates
Misra, Anup Kumar,Tiwari, Pallavi,Madhusudan, Soni Kamlesh
, p. 325 - 329 (2007/10/03)
An efficient per-O-acetylation of carbohydrates catalyzed by HClO 4-SiO2 is reported using a stoichiometric quantity of acetic anhydride avoiding the use of pyridine and excess acetic anhydride under solvent-free conditions.
