79384-19-3

Upstream product

• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 100-39-0 benzyl bromide 
• 133745-75-2 N-fluorobis(benzenesulfon)imide 
• 1423496-75-6 p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 160549-11-1 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose 
• 532959-21-0 2-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid benzyl ester 
• 532959-22-1 2-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid 
• 133857-94-0 2-S-(3',4',6'-tri-O-benzyl-2'-deoxy-α-D-arabino-hexopyranosyl)-5,5-dimethyl-1,3,2-dioxa-2-thiolo-2-thioxophosphorinane 
• 220284-26-4 3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetamidate 
• 129885-86-5 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl dimethylphosphinothioate 
• 2873-29-2 D-glucal triacetate 

Relevant academic research and scientific papers

Highly stereoselective synthesis of 2-deoxy-α- glycosides and α- disaccharides

Highly stereoselective synthesis of 2-deoxy-α-glycosides including disaccharides is described, using S-(2-deoxyglycosyl)phosphorodithioates as glycosyl donors, in the presence of silver perchlorate in acetonitrile.

Glycosyloxyselenation - Deselenation of Glycals: a New Approach to 2'-Deoxy-disaccharides

Glycosyloxyselenation of 3,4,6-tri-O-benzyl-D-glucal followed by reductive removal of the phenylseleno-group demonstrates the potential of a novel synthetic approach to 2'-deoxy-disaccharides.

Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions

The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.

Nitrogen-Centered Radical-Mediated Cascade Amidoglycosylation of Glycals

A nitrogen-centered radical-mediated strategy for preparing 1,2-trans-2-amino-2-deoxyglycosides in one step was established. The cascade amidoglycosylation was initiated by a benzenesulfonimide radical generated from NFSI under the catalytic reduction of TEMPO. The benzenesulfonimide radical was electrophilically added to the glycals, and then the resulting glycosidic radical was converted to oxocarbenium upon oxidation by TEMPO+, which enabled the following anomeric specific glycosylation.

Copper-Catalyzed Stereoselective Synthesis of 2-Deoxygalactosides

An efficient glycosylation method to synthesize 2-deoxy- O -galactosides based on a Cu(II)-catalyzed reaction without additional ligand has been developed. The glycosylation was amenable to different protected glycal donors and a wide range of acceptors including alcohols, amino acids, sugars, and phenol, and proceeds with excellent yield and high α-selectivity under mild conditions. The reaction proceeds readily on a gram scale, and its versatility is exemplified in the synthesis of oligosaccharides.

Stereoselective organocatalyzed glycosylations-thiouracil, thioureas and monothiophthalimide act as Br?nsted acid catalysts at low loadings

Thiouracil catalyzes stereoselective glycosylations with galactals in loadings as low as 0.1 mol%. It is proposed that in these glycosylations thiouracil, monothiophthalimide, and the previously reported catalyst, Schreiner's thiourea, do not operate via

Sterically Hindered 2,4,6-Tri- tert-butylpyridinium Salts as Single Hydrogen Bond Donors for Highly Stereoselective Glycosylation Reactions of Glycals

We demonstrate here that the strained and bulky protonated 2,4,6-tri-tert-butylpyridine salts serve as efficient catalysts for highly stereoselective glycosylations of various glycals. Moreover, the mechanism of action involves an interesting single hydrogen bond mediated protonation of glycals and not via the generally conceived Br?nsted acid pathway. The counteranions also play a role in the outcome of the reaction.

Additive-Free Gold(III)-Catalyzed Stereoselective Synthesis of 2-Deoxyglycosides Using Phenylpropiolate Glycosides as Donors

Stereoselective synthesis of deoxyglycosides has been achieved from benchtop stable and easily synthesizable deoxy-phenylpropiolate glycosides (D-PPGs) using gold(III) salt as catalyst under external additive-free conditions. Under a simple catalytic system, D-PPGs reacted with a variety of sugar and non-sugar acceptors to produce majorly α-stereoselective O/N-deoxyglycosides in good to excellent yields and regenerate easily separable and reusable phenylpropiolic acid. Deoxy-PPGs containing armed and disarmed groups survived well under the optimized reaction conditions. In addition, the orthogonal nature of D-PPGs was showcased, and 1,1′-linked trehalose-type sugar was also synthesized.

Stereoselective Synthesis of 2-Deoxyglycosides from Glycals by Visible-Light-Induced Photoacid Catalysis

The direct, photoacid-catalyzed synthesis of 2-deoxyglycosides from glycals is reported. A series of phenol-conjugated acridinium-based organic photoacids were rationally designed, synthesized, and studied alongside the commercially available phenolic catalyst eosin Y. In the presence of such a photoacid catalyst and light, synthetic glycals were activated and coupled with a range of alcohols to afford 2-deoxyglycosides in good yields and with excellent α-selectivity.

Secondary amine salt catalyzed controlled activation of 2-deoxy sugar lactols towards alpha-selective dehydrative glycosylation

A new organocatalytic glycosylation method exploiting the lactol functionality has been disclosed. The catalytic generation of glycosyl oxacarbenium ions from lactols under forcible conditions via weakly Br?nsted-acidic, readily available secondary amine salts affects the diastereoselective glycosylation of 2-deoxypyranoses and furanoses. This operationally simple iminium catalyzed activation of 2-deoxy hemi-acetals is a potential alternative to the existing cumbersome methods that need specialized handling. The mechanisms for this unique transformation and kinetic/thermodynamic effects have been discussed based on both experimental evidence and theoretical studies.