82231-38-7Relevant academic research and scientific papers
Cyclodextrin chemistry; Part I. Application of a regioselective acetolysis method for benzyl ethers
Angibeaud,Utille
, p. 737 - 738 (1991)
Regioselective acetolysis of cyclomaltohexaose perbenzyl ethers at C-6 with acetic anhydride in the presence of trimethylsilyl trifluoromethanesulfonate at low temperature constitutes an easy route to the C-6 acetylated intermediate 2. Futher transformati
KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation-oxidation in one pot
Gurawa, Aakanksha,Kumar, Manoj,Rao, Dodla S.,Kashyap, Sudhir
supporting information, p. 16702 - 16707 (2020/10/27)
A novel and efficient protocol for chemoselective deacetylation under ambient conditions was developed using catalytic KMnO4. The stoichiometric use of KMnO4 highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation-oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while preventing over-oxidation to acids. Use of inexpensive and readily accessible KMnO4 as an environmentally benign reagent and the ease of the reaction operation were particularly attractive, and enabled the controlled oxidation and facile cleavage of acetate in a preceding step. This journal is
New class of alkynyl glycoside analogues as tyrosinase inhibitors
Saehlim, Natthiya,Athipornchai, Anan,Sirion, Uthaiwan,Saeeng, Rungnapha
supporting information, (2020/06/01)
A new series of alkynyl glycoside analogues were designed and synthesized from cheap and a commercially available sugar by introduction of various alkynyl and alkyl groups at C-1 and C-6 positions of the sugar ring. The inhibitory abilities of alkynyl gly
Acid-Catalyzed O-Glycosylation with Stable Thioglycoside Donors
Lacey, Kristina D.,Quarels, Rashanique D.,Du, Shaofu,Fulton, Ashley,Reid, Nicholas J.,Firesheets, Austin,Ragains, Justin R.
supporting information, p. 5181 - 5185 (2018/09/12)
Two classes of thioglycoside, 4-(4-methoxyphenyl)-3-butenylthioglycosides (MBTGs) and 4-(4-methoxyphenyl)-4-pentenylthioglycosides (MPTGs), undergo acid-catalyzed O-glycosylations with a range of sugar and nonsugar alcohols at 25 °C. Electron density at t
Isopropenyl acetate: A cheap and general acylating agent of alcohols under metal-free conditions
Temperini, Andrea,Minuti, Lucio,Morini, Tommaso,Rosati, Ornelio,Piazzolla, Francesca
, p. 4051 - 4053 (2017/09/27)
Functionalized primary, secondary and tertiary alcohols are efficiently acetylated by isopropenyl acetate and catalytic p-TsOH.
Regioselective acetolysis of highly O-benzylated carbohydrates promoted by iodine or an iodine/silane combined reagent: Use of isopropenyl acetate as an alternative to acetic anhydride
Giordano, Maddalena,Iadonisi, Alfonso,Pastore, Antonello
, p. 3137 - 3147 (2013/06/27)
Regioselective acetolytic de-O-benzylation of poly-O-benzylated sugars can be triggered by the activation of isopropenyl acetate (IPA) with either an iodine/silane combined reagent or iodine alone. Unlike other known acetolysis procedures, the protocols p
Synthesis of esters derived from 2,3,4-tri-O-benzyl-α-D- methylglucoside
Pinto, Tiago A.D.,Hrdina, Radim,Kirsch, Gilbert,Oliveira-Campos, Ana M.F.,Rodrigues, Ligia M.,Esteves, Ana P.
experimental part, p. 185 - 193 (2012/05/05)
2,3,4-Tri-O-benzyl-α-D-methylglucoside was prepared and reacted with several acids: benzoic, phenylacetic, 2-(3-bromo-propoxy)-benzoic, acetylsalicylic and 4-(toluene-4-sulfonylamino)-benzoic. The products were isolated with low to fair yields and fully c
Bromodimethylsulfonium bromide-silver triflate: A new powerful promoter system for the activation of thioglycosides
Xiong, De-Cai,Zhang, Li-He,Ye, Xin-Shan
supporting information; experimental part, p. 1696 - 1700 (2009/07/18)
Bromodimethylsulfonium bromide (BDMS) in combination with silver triflate provides a very efficient thiophilic promoter system, capable of activating both "disarmed" and "armed" thioglycosides for glycosidic bond formation. The usefulness of this new prom
A stable, commercially available sulfenyl chloride for the activation of thioglycosides in conjunction with silver trifluoromethanesulfonate
Crich, David,Cai, Feng,Yang, Fan
, p. 1858 - 1862 (2008/12/22)
p-Nitrobenzenesulfenyl chloride is a stable commercially available sulfenyl chloride that, in conjunction with silver triflate, cleanly activates a wide range of thioglycosides for glycosylation at -78 °C in CH2Cl2.
SbCl3 as a highly efficient catalyst for the acetylation of alcohols, phenols, and amines under solvent-free conditions
Bhattacharya, Asish K.,Diallo, Mamadou A.,Ganesh, Krishna N.
, p. 1518 - 1526 (2008/09/20)
Antimony trichloride has been found to be an efficient and expedient catalyst for the acylation of alcohols, phenols, amines, and sugars with acetic anhydride in high yields and in a short reaction time under solvent-free conditions at room temperature. Also, racemization of chiral alcohols and epimerization of sugars were not observed in any of the substrates. Copyright Taylor & Francis Group, LLC.
