56225-80-0Relevant articles and documents
Highly efficient β-glucosylation of the acidic hydroxyl groups, phenol and carboxylic acid, with an peracetylated glucosyl fluoride using a combination of BF3·Et2O and DTBMP as a promoter
Oyama, Kin-Ichi,Kondo, Tadao
, p. 1627 - 1629 (1999)
A combination of BF3·Et2O and DTBMP was established to be an efficient promoter of β-glucosylation of both phenols and carboxylic acids with a peracetylated glucosyl fluoride (2). This new method achieved remarkably high yields and β
Polyvinyl trisulfonate ethylamine based solid acid catalyst for the efficient glycosylation of sugars under solvent free conditions
Chaugule, Avinash A.,Jadhav, Amol R.,Kim, Hern
, p. 104715 - 104724 (2015/12/30)
Heterogeneous Bronsted solid acid catalysts have the potential to decrease the environmental impact related to chemical production. Herein, we have synthesized polyvinyl bound trisulfonate ethylamine chloride (PV-THEAC) and polyvinyl bound disulfonate ethylamine (PV-DSEA) as Bronsted solid acid catalysts which exhibited effective catalytic activity for acid catalyzed glycosylation reactions with sugar derivatives. In particular, 0.3 equiv. of the PV-THEAC catalyst was found to be the most efficient and a reusable catalyst for glycosylation reactions. A high density of the trisulfonic group (-OSO3H) contributed to the excellent catalytic activity during glycosylation. Moreover, glycosylation reactions with d-mannose, d-xylose and d-glucose have been studied with alcohol. Remarkable acceleration of the glycosylation reaction using a glycosyltrichloroacetimidate donor was obtained with the selective production of β-glycoside.
Phyllanthoside-Phyllanthostatin Synthetic Studies. 8. Total Synthesis of (+)-Phyllanthoside. Development of the Mitsunobu Glycosyl Ester Protocol
Smith III, Amos B.,Rivero, Ralph A.,Hale, Karl J.,Vaccaro, Henry A.
, p. 2092 - 2112 (2007/10/02)
The first total syntheses of the antineoplastic glycoside (+)-phyllanthoside (1) and the parent disaccharide (-)-phyllanthose (5) have been achieved. Stereoselective Koenigs-Knorr coupling of two 6-deoxyglucose derivatives, bromide 54 and alcohol 55, generated the uncommon 1′ → 2β glycosidic linkage of (-)-phyllanthose. A stereochemically convergent Mitsunobu reaction of protected disaccharide 87 with aglycon carboxylic acid 80, prepared via asymmetric synthesis, then led to 1 of high enantiomeric purity. The Mitsunobu procedure comprises an efficient general method for stereospecific assembly of β-glycosyl esters.
2-(Trimethylsilyl)ethyl Glycosides. Synthesis, Anomeric Deblocking, and Transformation into 1,2-Trans 1-O-Acyl Sugars
Jansson, Karl,Ahlfors, Stefan,Frejd, Torbjoern,Kihlberg, Jan,Magnusson, Goeran,et al.
, p. 5629 - 5647 (2007/10/02)
Twenty-seven mono --> tetrasaccharidic 2-(trimethylsilyl)ethyl (TMSET) glycosides were synthesized by the Koenigs-Knorr-type method in combination with a wide range of standard reagents for glycoside synthesis and protecting-group chemistry.Variously protected TMSET glycosides were treated with BF3*Et2O (0.7-0.8 equiv) and different carboxylic anhydrides (1.1-15 equiv) in toluene at 22-55 deg C, which gave in one step the corresponding protected 1-O-acyl sugars.In the majority of cases, the yields of purified compounds exceeded 90percent and the anomeric configuration of the starting TMSET glyoside was conserved to a large extent (>95percent) in most of the 1-O-acylated products.Unprotected and acetyl-, benzoyl-, benzyl-, dimethyl-tert-butylsilyl-, and phthaloyl-protected mono-->tetrasaccharidic TMSET glycosides were anomerically deblocked by using trifluoroacetic acid in dichloromethane at 0-22 deg C for 10-30 min.The hemiacetal products were isolated in 88-96percent yield; all reagents and byproducts were volatile and easily removed.
Synthesis of Glycosyl Trifluoroacetates and Their Reactions with Carboxylic Acids
Kobayashi, Miyuki,Shimadate, Toshisada
, p. 4069 - 4074 (2007/10/02)
2,3,4,6-Tetra-O-acetyl-1-O-trifluoroacetyl-α-D-glucopyranose was prepared in high yield by treating 1,2,3,4,6-penta-O-acetyl-α- or -β-D-glucopyranose with a mixture of trifluoroacetic acid and its anhydride in the presence of trifluoromethanesulfonic acid or antimony (V) fluoridegraphite catalyst.The reaction of the trifluoroacetate with some carboxylic acids afforded the corresponding 1-O-acyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoses.By a similar procedure, anomeric 1-O-trifluoroacetyl-2,3,5-tri-O-benzoyl- and -2,3,5-tri-O-acetyl-D-ribofuranose were obtained from 1-O-acetyl-2,3,5-tri-O-benzoyl- and 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose respectively, and these trifluoroacetates were allowed to react with some carboxylic acids to yield the corresponding 1-O-acyl-β-D-ribofuranose benzoates and acetates.These products were also prepared by direct fusion of 1-O-acetyl-β-D-ribofuranose benzoate and acetate with carboxylic acids.Keywords-glycosyl trifluoroacetate; glycosyl carboxylate; fusion reaction; tetra-O-acetyl-α-D-glucopyranosyl trifluoroacetate; tri-O-benzoyl-α,β-D-ribofuranosyl trifluoroacetate; tri-O-acetyl-α,β-D-ribofuranosyl trifluoroacetate
AN EFFICIENT SYNTHESIS OF GLYCOSYL ESTERS EXPLOITING THE MITSUNOBU REACTION.
Smith III, Amos B.,Hale, Karl J.,Rivero, Ralph A.
, p. 5813 - 5816 (2007/10/02)
The anomeric hydroxyl group of various pyranose hemiacetals can be esterified with inversion of configuration, conveniently, mildly and on large-scale using triphenylphosphine (TPP), with either diisopropylazodicarboxylate (DIAD) or diethylazodicarboxylat
