61474-60-0

Upstream product

• 709-83-1 2-(cyclohexyloxy)tetrahydro-2H-pyran 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 108-93-0 cyclohexanol 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 1037310-33-0 1,4-bis(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)benzene 
• 1037310-30-7 1,4-bis(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)-2,3,5-trimethylbenzene 
• 872123-62-1 2,4-dinitro-6-(methoxycarbonyl)phenyl 2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranoside 
• 90357-89-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 193953-69-4 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl diethyl phosphite 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl fluoride 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 

Relevant academic research and scientific papers

A novel greener glycosidation using an acid-ionic liquid containing a protic acid

The glycosidations of glucopyranosyl diethyl phosphite and alcohols using an ionic liquid, 1-n-hexyl-3-methylimidazolium trifluoromethanesulfonimidide (C6mim[NTf2]) containing a protic acid, trifluoromethanesulfonimide (HNTf2/s

Catalytic and stereoselective glycosylation with glycosyl fluoride using active carbocationic species paired with tetrakis(pentafluorophenyl)borate or trifluoromethanesulfonate

Catalytic and stereoselective glycosylation with glycosyl fluoride using carbocationic species paired with tetrakis(pentafluorophenyl)borate [B(C6F5)4-] or trifluoromethanesulfonate (TfO-) is investigated. When the glycosylation is carried out using the former catalyst in dichloromethane containing tBuCN, the major product is β-glycoside while α-selectivity is observed when the latter catalyst in dichloromethane containing Et2O is used. In addition to the characteristic properties of the solvent, the nature of the counter anion such as B(C6F5)4- or TfO- plays important roles in controlling the selectivity. Thus, an appropriate combination of catalyst and solvent leads to the formation of disaccharides.

A stereoselective ring-closing glycosylation via nonglycosylating pathway

Two glycosyl partners were first coupled with as ester linkage, which upon reductive acetylation produced an α-acetoxy ether group. The subsequent activation with TfOH triggered the ring-closing process and provided the corresponding glycosidic bond in high β-selectivity without relying on neighboring group participation.

Combined Lewis acid and Br?nsted acid-mediated reactivity of glycosyl trichloroacetimidate donors

Biomimetic conditions for a synthetic glycosylation reaction, inspired by the highly conserved functionality of carbohydrate active enzymes, were explored. At the outset, we sought to generate proof of principle for this approach to developing catalytic systems for glycosylation. However, control reactions and subsequent kinetic studies showed that a stoichiometric, irreversible reaction of the catalyst and glycosyl donor was occurring, with a remarkable rate variance depending upon the structure of the carboxylic acid. It was subsequently found that a combination of Br?nsted acid (carboxylic acid) and Lewis acid (MgBr2) was unique in catalyzing the desired glycosylation reaction. Thus, it was concluded that the two acids act synergistically to catalyze the desired transformation. The role of the catalytic components was tested with a number of control reactions and based on these studies a mechanism is proposed herein.

Oxidatively induced glycosylation starting from hydroquinone glycosides

As a new class of glycosyl donors, hydroquinone glycosides can be used for glycosylation reactions. Their activation can be performed either electrochemically or under homogeneous chemical conditions. Conventionally, several glucosides were produced with yields greater than 77% using DDQ in CH2Cl2 as oxidizing agent. For electrolyses, glycosides of trimethylhydroquinone are preferably used because their low oxidation potentials allow the utilization of an undivided cell. The synthesis of the glycosyl donors was achieved with high efficiency by direct coupling of the phenols with peracetylated monosaccharides employing boron trifluoride etherate as the catalyst. The oxidation of hydroquinone derivatives can also be applied to the generation of other stabilized cations.

Reconsidering glycosylations at high temperature: Precise microwave heating

Current methods for glycosylation of complex alcohols, e.g. with glycosyl trichloroacetimidates, generally occur in the presence of a strong Lewis acid 'promoter', and at sub-ambient temperatures. However, the older literature reports high-temperature gly

Generation of alkoxycarbenium ion pools from thioacetals and applications to glycosylation chemistry

(Chemical Equation Presented) Alkoxycarbenium ions have been generated and accumulated as "cation pools" by the low-temperature electrochemical oxidation of α-phenylthioethers. Although an unsuccessful attempt to accumulate glycosyl cations was made, a one-pot method for electrochemical glycosylation, which involves anodic oxidation of thioglycosides to generate glycosyl cation equivalents followed by their reactions with glycosyl acceptors, has been developed.

Dehydrative glycosylation by diethylaminosulfur trifluoride (DAST) - tin(II) trifluoromethanesulfonate-tetrabutylammonium perchlorate - triethylamine system

Dehydrative glycosylation using 2,3,4,6-tetra-O-benzyl-D-glucopyranose was carried out by the use of a condensing reagent system composed of diethylaminosulfur trifluoride (DAST), tin(II) triflate, tetrabutylammonium perchlorate, and triethylamine. Using this system, two tetrasaccharides, O- a-D-glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→3)-Oα-D-glucopyranosyl- (1→4)-D-glucopyranose and O-a-D-glucopyranosyl-(1→3)-O-α-D- glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→4)-D-glucopyranose, were synthesized.

A novel intramolecular decarboxylative glycosylation via mixed carbonate

A two-step glycosylation procedure, which involves (1) linking two sugars by using carbonate as a connector, (2) removing carbon dioxide to form a glycosidic bond by the aid of Lewis acid, has been developed. This glycosylation procedure was based on the opposite mode of connection, where a glycosyl acceptor was activated to link sugars.