79384-22-8

Basic information

• Product Name: O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1[*]6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• Synonyms: O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1[*]6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• CAS NO: 79384-22-8
• Molecular Weight: 676.804
• Mol File: 79384-22-8.mol
• Article Data: 32

Chemical Properties

• CAS DataBase Reference: O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1[*]6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1[*]6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose(79384-22-8)
• EPA Substance Registry System: O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1[*]6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose(79384-22-8)

Safety Data

• Hazardous Substances Data: 79384-22-8(Hazardous Substances Data)

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 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 220284-26-4 3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetamidate 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 1423496-75-6 p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside 
• 2873-29-2 D-glucal triacetate 
• 100-39-0 benzyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 253197-57-8 C₁₂H₁₉O₆^(1-)*K⁽¹⁺⁾ 
• 71001-09-7 1,2:3,4-di-O-isopropylidene-6-O-trifluoromethanesulfonyl-α-D-galactopyranose 
• 160549-11-1 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose 
• 125135-29-7 3,4,6-tri-O-benzyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranoside 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 121388-85-0 tri-O-benzyl-α-D-glucopyranose-(1,2-t-butylorthoacetate) 

Relevant articles and documents

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.

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.

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.