83921-79-3

Basic information

• Product Name: allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside
• Synonyms: allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside
• CAS NO: 83921-79-3
• Molecular Weight: 490.596
• Mol File: 83921-79-3.mol

Chemical Properties

• CAS DataBase Reference: allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside(83921-79-3)
• EPA Substance Registry System: allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside(83921-79-3)

Safety Data

• Hazardous Substances Data: 83921-79-3(Hazardous Substances Data)

Upstream product

• 79218-68-1 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose 
• 107-18-6 allyl alcohol 
• 2595-07-5 allyl β-D-glucopyranoside 
• 100-44-7 benzyl chloride 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 88999-17-1 allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 51532-75-3 3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose 
• 90365-70-1 C₃₂H₃₆O₇ 
• 3254-16-8 3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose 
• 53270-12-5 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose 
• 125135-29-7 3,4,6-tri-O-benzyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranoside 
• 2873-29-2 D-glucal triacetate 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 100-39-0 benzyl bromide 

Downstream Products

• 93495-91-1 O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-D-glucopyranose 
• 93495-91-1 O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-D-glucopyranose 
• 88988-47-0 Acetic acid (2S,3R,4S,5R,6R)-2-((2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 90302-53-7 Trifluoro-methanesulfonic acid (2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 929619-07-8 allyl 3,4,6-tri-O-benzyl-2-O-p-methoxybenzyl-β-D-glucopyranoside 
• 959925-58-7 carboxymethyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-2-O-lactone 
• 1343987-70-1 allyl 2-pivaloyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 1343988-82-8 allyl 3-O(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-O-6-O-(4-methoxyphenol)-α-D-glycopyranoside 
• 1343987-71-2 2-pivaloyl-3,4,6-tri-O-benzyl-β-D-glucopyranose 
• 1343987-75-6 allyl 2-O-benzyl-3-O(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glycopyranoside 
• 1343987-72-3 allyl 3-O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-4,6-O-benzylidene-α-D-glucopyranoside 

Relevant articles and documents

Simple and mild stereoselective O-glycosidation using 1,2-anhydrosugars under neutral conditions

The ring opening of α-D-1,2-anhydrohexapyranoses with phenols proceeded smoothly in ethyl acetate (neutral conditions) in the absence of metal ion catalysts or additives to stereoselectively furnish 1,2-cis-α-aryl glycosides as the major product and 1,2-t

Synthesis of Staphylococcus aureus type 5 capsular polysaccharide repeating unit using novel l-FucNAc and d-FucNAc synthons and immunochemical evaluation

Staphylococcus aureus is a major cause of nosocomial infections. Glycoconjugates of type 5 and 8 capsular polysaccharides have been investigated for vaccine application. The proposed structure of type 5 polysaccharide is: →4-β-d-ManNAcA-(1→4)-α-l-FucNAc(3OAc)-(1→3) -β-d-FucNAc-(1→. The stereocontrolled insertion of these three glycosydic bonds is a real synthetic challenge. In the present paper we report the preparation of two novel versatile l- and d-fucosamine synthons from commercially available starting materials. In addition we applied the two building blocks to the synthesis of type 5 trisaccharide repeating unit. The immunochemical properties of the synthesized trisaccharide were assessed by competitive ELISA and by immunodot blot analysis using sera of mice immunized with type 5 polysaccharide conjugated to CRM197. The results suggest that although the type 5 S. aureus trisaccharide is recognized by specific anti polysaccharide antibodies in dot blot, structures longer than the trisaccharide may be needed in order to significantly compete with the native type 5 polymer in the binding with sera from mice immunized with S. aureus type 5 polysaccharide-CRM197 conjugate.

SYNTHETIC OLIGOSACCHARIDES FOR MORAXELLA VACCINE

The present invention provides synthetic Moraxella catarrhalis lipooligosaccharide (LOS)-based oligosaccharides and conjugates containing various M. catarrhalis serotype-specific oligosaccharide antigens or various core M. catarrhalis oligosaccharide structures or motifs corresponding to one or more of the three major serotypes and/or members within a given serotype. The oligosaccharides may be synthesized by a chemical assembly methodology relying on a limited number of monosaccharide and disaccharide building blocks. The invention further provides M. catarrhalis LOS-based immunogenic and immunoprotective compositions and antibodies derived therefrom for diagnosing, treating, and preventing infections caused by M. catarrhalis.

Synthesis and immunochemical characterization of 5-linked glycoconjugate vaccines against Candida albicans

Replacement of the glycoside oxygen atom by a sulphur atom is a promising technique for creating glycoconjugates with increased resistance to hydrolysis by endogenous glycosidases. The synthesis and antigenic properties of two distinct (1 →2)-β-mannan trisaccharides with inter residue-S-linked mannopyranose residues are described. Syntheses were based on an oxidationreduction strategy to construct the O-_linked β-mannopyranoside bonds and a SN2 inversion to provide 1-thio-β-mannopyranoside residues. Subsequently the allyl trisaccharide glycosides were subjected to photo addition with cysteine amine and coupled to tetanus toxoid and bovine serum albumin with good efficiency via an adipic acid tether. Rabbit immunization studies revealed that the antibodies elicited by the two glycoconjugates were able to recognize the corresponding O-linked trisaccharide epitope conjugated to BSA and the native cell wall antigen of Candida albicans.

Carboxymethylglycoside lactones (CMGLs): structural variations on the carbohydrate moiety

New glucose and galactose based bicyclic lactones, with variations in the anomeric configuration, the protecting groups (acetyl or benzyl) and the furanosyl or pyranosyl rings were synthesized from allyl glycosides and used for the preparation of a series

A convenient multigram preparation of functionalized 2-azido-2-deoxy-D-mannose as a useful orthogonally protected building block for oligosaccharide synthesis

Multigram preparation of strategically protected 2-azido-2-deoxy mannose 5 from pentaacetyl glucose 1 is described. This manno-derivative was obtained in a straightforward manner and in high overall yield and represents a flexible building-block for complex oligosaccharide synthesis.

Synthesis of a beta1,2-mannopyranosyl tetrasaccharide found in the phosphomannan antigen of Candida albicans.

The synthesis of a portion of the challenging beta1,2-mannosyl polymer found in the cell walls of Candida albicans was undertaken to develop a conjugate vaccine against C. albicans and to facilitate NMR conformational studies of this unique polysaccharide

Synthesis of sulfated trisaccharide ligands for the selectins

In a directed effort to elucidate the molecular factors responsible for selectin-mediated cell adhesion events as a basis for the generation of potent and specific inhibitors of these processes, we have synthesized a variety of sulfated analogs of the trisaccharide recognition epitopes Lewis a [Lea: Ga1β1→3(Fucα1→4)GlcNAc] and Lewis x [Le(x): Galβ1→4(Fucαl→3)GlcNAc]. Our divergent synthetic route allows for the synthesis of gram quantities of these sulfated trisaccharides from common intermediates in 10-20% overall yields and in no more than 15 linear steps. In addition, we have anchored the reducing end of the Lea and Le(x) trisaccharide precursors with a β- allyl aglycone, providing a single anomer of each final product and allowing for further modification into multivalent derivatives.

An efficient stereoselective synthesis of enantiomerically pure mono- and di-O-hexadecyl-β-D-glucosylglycerol ethers by epoxidation of an allyl β-D-glucopyranaside asymmetrically induced by the glucide moiety

1-O-Hexadecyl and 1,2-di-O-hexadecyl-3-O-(β-D-glucopyranosyl)-sn-glycerol ethers were obtained by regiospecific opening of the oxirane ring of the 2',3'-epoxypropyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside synthetized by stereoselective epoxidati

Diastereoselective Bromination of Allyl Glycosides Using Tetrabutylammonium Tribromide

Both (R) and (S)-2,3-dibromo-1-propanol with e.e. up to 60percent have been obtained by diastereoselective addition of Br2 to allyl glucosides and galactosides having only one unprotected hydroxyl group at C-2 or C-6 using tetrabutylammonium tribromide, followed by hydrolysis.The absolute configuration is shown to depend on the position of the free hydroxyl and on the configuration at the anomeric centre.