39698-00-5

Usage

Uses

Used in Organic Chemistry Research:
1,2,4,6-Tetra-O-acetyl-3-O-allyl-beta-D-glucopyranose is used as a synthetic intermediate for the preparation of complex carbohydrate structures and glycosides, facilitating the development of new organic compounds with potential applications in various fields.
Used in Biochemistry Research:
In biochemistry, 1,2,4,6-Tetra-O-acetyl-3-O-allyl-beta-D-glucopyranose is used as a key component in the synthesis of biologically active molecules, contributing to the advancement of pharmaceuticals and other therapeutic agents.
Used in Pharmaceutical Development:
1,2,4,6-Tetra-O-acetyl-3-O-allyl-beta-D-glucopyranose is utilized as a building block in the creation of novel pharmaceuticals, particularly those targeting carbohydrate-based drug discovery, due to its unique structure and reactivity.
Used in Carbohydrate Molecular Manipulation:
1,2,4,6-Tetra-O-acetyl-3-O-allyl-beta-D-glucopyranose serves as a valuable tool in the study and manipulation of carbohydrate molecules, enabling researchers to explore the intricate relationships between carbohydrates and their biological functions or interactions with other molecules.

InChI:InChI=1/C17H24O10/c1-6-7-22-15-14(24-10(3)19)13(8-23-9(2)18)27-17(26-12(5)21)16(15)25-11(4)20/h6,13-17H,1,7-8H2,2-5H3/t13-,14+,15-,16-,17+/m0/s1

Upstream product

• 108-24-7 acetic anhydride 
• 91109-44-3 3-O-allyl-D-glucopyranose 
• 20316-77-2 (3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole 
• 350254-95-4 3-O-allyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 46398-94-1 (2S,3R,4R,5R)-4-Allyloxy-5-((R)-1,2-dihydroxy-ethyl)-tetrahydro-furan-2,3-diol 
• 77388-91-1 3-O-allyl-β-D-glucopyranoside 

Downstream Products

• 103130-11-6 benzyl 3-O-allyl-2,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 197005-22-4 phenyl 2,4,6-tri-O-acetyl-3-O-allyl-1-thio-β-D-glucopyranoside 
• 502181-48-8 phenyl 3-O-allyl-2,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside 
• 93661-22-4 benzyl 4-O-(2-O-acetyl-3-O-allyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-β-D-galactopyranoside 
• 93661-24-6 benzyl 4-O-(3-O-allyl-4,6-O-benzylidene-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-β-D-galactopyranoside 
• 93661-30-4 benzyl O-β-D-glucopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside 
• 93661-25-7 benzyl 4-O-(2-O-acetyl-3-O-allyl-4,6-O-benzylidene-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-β-D-galactopyranoside 
• 93661-28-0 benzyl O-β-D-glucopyranosyl-(1->2)-O-(3-O-allyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside 
• 93661-29-1 benzyl O-β-D-glucopyranosyl-(1->2)-O-(3-O-allyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside 
• 93661-27-9 benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->2)-O-(3-O-allyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside 
• 93661-23-5 benzyl 4-O-(3-O-allyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-β-D-galactopyranoside 
• 93661-21-3 benzyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranosyl)-β-D-galactopyranoside 
• 1422650-00-7 2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-β-D-glucopyranoside 
• 1422649-99-7 2-(trimethylsilyl)ethyl 3-O-allyl-2,6-di-O-benzyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

First Total Synthesis of Trehalose-Containing Branched Oligosaccharide OSE-1 of Mycobacterium gordonae (Strain 990)

The first total synthesis of the branched oligosaccharide OSE-1 of Mycobacterium gordonae (strain 990) is reported. An intramolecular aglycon delivery approach was used for constructing the desymmetrized 1,1′-α,α-linked trehalose moiety. A [3+2] glycosylation of the trisaccharide donor and trehalose acceptor furnished the right hand side pentasaccharide. Regioselective O3 glycosylation of L-rhamnosyl 2,3-diol allowed expedient synthesis of the left hand side tetrasaccharide. The nonasaccharide was assembled in a highly convergent fashion through a [4+5] glycosylation. Take the strain: First total synthesis of the branched oligosaccharide OSE-1 of Mycobacterium gordonae (strain 990) is reported. An intramolecular aglycon delivery approach was used for constructing the desymmetrized 1,1′-α,α-linked trehalose moiety. Regioselective O3 glycosylation of L-rhamnosyl 2,3-diol allowed expedient synthesis of the left hand side tetrasaccharide. The nonasaccharide was assembled in a highly convergent fashion through a [4+5] glycosylation.

Synthesis and NMR elucidation of four novel 2-(trimethylsilyl)ethyl glycosides

Four novel 2-(trimethylsilyl)ethyl glycosides have been synthesized by a short and efficient route starting from d-glucose. Their structures were elucidated by applying high-resolution mass spectra, and one-dimensional and two-dimensional NMR techniques.

Carbohydrate-based scaffolds for the generation of sortiments of bioactive compounds

The polyfunctionality and conformational rigidity of carbohydrates make this class of compounds ideal scaffolds for the production of sortiments1 of bioactive compounds. Examples of carbohydrate-derived peptidomimetics of biological interest, such as somatostatin agonists and integrin antagonists, are presented. In order to have access to solid phase supported sortiments of compounds, orthogonally protected or unprotected carbohydrates were linked to polymers and reacted in the solid phase employing different regioselective strategies. Original bicyclic and tricyclic glycidic scaffolds were easily obtained starting from natural sugars such as D-arabinose and D-fructose. Manipulation of these conformationally blocked compounds afforded different carbohydrate-based derivatives, among which azidoacids are useful precursors of β-turn peptidomimetics.

Total synthesis of the Glc3Man N-glycan tetrasaccharide

The total synthesis of the tetrasaccharide Glcα(1→2)Glcα(1→3)Glcα(1→3)ManαOMe, which corresponds to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved by the use of differentially protected selenoglycosides and thioglycosides as glycosyl donors, all of which possessed non-participating protection of the 2-hydroxyl group. Favourable anomeric stereoselectivity was achieved for the glycosylation reactions by the use of ether as solvent, or co-solvent. Global deprotection by catalytic hydrogenation with palladium acetate in a mixture of ethanol and acetic acid yielded the target tetrasaccharide.

Dehydrative Glycosylation Using Heptabenzyl Derivatives of Glucobioses and Lactose

Dehydrative glycosylations of the 2-, 3-, 4-, and 6-OH groups of D-glucopyranose with hepta-O-benzyl derivatives of glucobioses (O-D-glucopyranosyl-(1->n)-D-glucopyranose; n = 2, 3, 4, or 6) and lactose, in the presence of a ternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine in dichloromethane showed that the selectivity of the reaction depended on the anomeric configuration and the linking position to the reducing tribenzylglucose moiety of the nonreducing tetrabenzylglucosyl residue and on the class of the OH group to be glycosylated.The use of a quaternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine made all but the β(1->2)-linked biosyl donor undergo α-condensation.Several new linear trisaccharides were obtained via debenzylation of the condensates.

SYNTHESIS OF LYCOTETRAOSE

The title tetrasaccharide, namely, O-β-D-glucopyranosyl-(1->2)-O-3)>-O-β-D-glucopyranosyl-(1->4)-D-galactose, has been synthesized by Koenigs-Knorr type of condensations in a stepwise manner by way of the preparation of the di- and

Syntheses of Acetylated Trisaccharides, Manαl->3Mnaβl->GlcNAc and Manαl->2Manβl->4ClcNAc, relating to Mannosidosis

The title trisaccharides (22 and 30) were synthesized by stepwise condensation of suitably protected monosacchride units. 3-O-Allyl-2-O-benzoyl-4,6-di-O-benzyl-α-D-glucopyranosyl bromide (9) and 2-acetamido-1,6-anhydro-3-O-benzyl-2-deoxy-β-D-glucopyranose