79384-22-8

Upstream product

• 51532-76-4 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 135192-35-7 O-(3,4,6-tri-O-benzyl-2-O-<(pentafluorophenoxy)thiocarbonyl>-β-D-glucosyl)-(1<*>6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 121399-46-0 1,2:3,4-di-O-isopropylidene-6-O-(3,4,6-tri-O-benzyl-2-O-(methylthio)thiocarbonyl-β-D-glucopyranosyl)-α-D-galactopyranose 
• 124718-67-8 6'-(1',2':3',4'-diisopropylidenegalactopyranosyl) 3,4,6-tri-O-benzyl-2-deoxy-2-(phenylthio)-β-D-glucopyranoside 
• 144100-97-0 (3aR,5R,5aS,8aS,8bR)-5-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(4-methoxy-phenylsulfanyl)-tetrahydro-pyran-2-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 129885-86-5 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl dimethylphosphinothioate 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 243142-16-7 6-[2-S-(1'-acetyl-2'-methylethenyl)-3,4,6-tri-O-benzyl-2-thio-β-D-glucopyranosyl]-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 
• 220284-26-4 3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetamidate 
• 532959-22-1 2-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 532959-21-0 2-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid benzyl ester 
• 152420-91-2 1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-α-D-glucopyranose 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

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.

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.

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.

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.

TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.

Reagent-Controlled Stereoselective Glycosylation

Provided are methods for the efficient stereoselective formation of glycosidic bonds, without recourse to prosthetic or directing groups.

A reagent-controlled SN2-glycosylation for the direct synthesis of β-linked 2-deoxy-sugars

The efficient and stereoselective construction of glycosidic linkages remains one of the most formidable challenges in organic chemistry. This is especially true in cases such as β-linked deoxy-sugars, where the outcome of the reaction cannot be controlled using the stereochemical information intrinsic to the glycosyl donor. Here we show that p-toluenesulfonic anhydride activates 2-deoxy-sugar hemiacetals in situ as electrophilic species, which react stereoselectively with nucleophilic acceptors to produce β-anomers exclusively. NMR studies confirm that, under these conditions, the hemiacetal is quantitatively converted into an α-glycosyl tosylate, which is presumably the reactive species in the reaction. This approach demonstrates that use of promoters that activate hemiacetals as well-defined intermediates can be used to permit stereoselective glycosylation through an SN2-pathway.

Highly stereoselective glycosyl-chloride-mediated synthesis of 2-deoxyglucosides

Cl intermediates: The glycosylation of per-O-benzylated 2-deoxy- and 2,6-dideoxythioglycosides, promoted by the combination of para-toluenesulfenyl chloride (p-TolSCl) and silver triflate (AgOTf), furnished the products in high yields and high stereoselec

The synthesis of 2-deoxy-α-d-glycosides from d-glycals catalyzed by TMSI and PPh3

2-Deoxyglycosides were synthesized in high α-selectivity by the direct addition of alcohols to d-glucal and d-galactal catalyzed by TMSI and PPh3. The acid labile isopropylidene group is tolerated under this condition.