31022-29-4

Upstream product

• 23392-28-1 methyl 3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 
• 65877-18-1 methyl 4,6-O-benzylidene-2,3-O-(dibutyl-stannylidene)-α-D-mannopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 100-52-7 benzaldehyde 
• 63167-69-1 methyl 2,3-O-isopropylidene-α-D-mannopyranoside 
• 73395-14-9 methyl (R,R)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 4148-71-4 methyl (exo-Ph)-2,3: 4,6-di-O-benzylidene-α-D-mannopyranoside 
• 2774-19-8 (2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 

Downstream Products

• 80599-55-9 methyl 3,6-di-O-benzyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-mannopyranoside 
• 79218-81-8 methyl 4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,6-di-O-benzyl-α-D-mannopyranoside 
• 79218-82-9 methyl 2,4-di-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,6-di-O-benzyl-α-D-mannopyranoside 
• 80612-72-2 methyl 4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-α-D-mannopyranoside 
• 83738-43-6 methyl 3,6-di-O-benzyl-2,4-di-O-methyl-α-D-mannopyranoside 
• 79218-93-2 methyl 2,4-di-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

A NOVEL REDUCTIVE RING-OPENING OF CARBOHYDRATE BENZYLIDENE ACETALS

Further examples are given of a facile, highly regioselective, reductive opening of benzylidene acetals of hexopyranosides using sodium cyanoborohydride-hydrogen chloride.For dioxolane benzylidene acetals, the direction of reductive opening of the five-me

One-pot synthesis of orthogonally protected sugars through sequential base-promoted/acid-catalyzed steps: A solvent-free approach with self-generation of a catalytic species

A varied set of solvent-free, one-pot synthetic sequences were developed to carry out the orthogonal protection of saccharide polyols. These sequences are composed of an initial regioselective benzylation, silylation or iodination (under mildly basic cond

Regioselective mono and multiple alkylation of diols and polyols catalyzed by organotin and its applications on the synthesis of value-added carbohydrate intermediates

A catalytic amount of dibutyltin dichloride was used to develop regioselective alkylation of diols and multiple alkylation of polyols. Alkyl groups, including allyl, alkynyl and long-chain alkyl groups, were successfully introduced to one or two hydroxyl

Tin-mediated regioselective benzylation and allylation of polyols: Applicability of a catalytic approach under solvent-free conditions

The first catalytic version of the stannylene-mediated benzylation and allylation of polyols is reported. The methodology is based on a simple solvent-free protocol that significantly advances, in terms of both experimental ease and synthetic scope, the a

Halide promoted organotin-mediated carbohydrate benzylation: Mechanism and application

In the present study, the mechanistic origin of the promoted organotin-mediated carbohydrate benzylation by halides was explored by the comparison of the activation ability of halides on benzylation of methyl β-d-galactoside. It was demonstrated that the

Direct selective and controlled protection of multiple hydroxyl groups in polyols via iterative regeneration of stannylene acetals

A direct selective protection (O-benzylation) of two or more hydroxyl groups in polyols displaying diverse structural patterns was made possible by the establishment of conditions that enable an efficient turnover for the Bu2Sn group, initially

Synthesis of novel mannose-based crown ethers

A novel class of chiral crown ether analogues incorporating carbohydrate subunits can be easily prepared from methyl α-D-mannopyranoside. By a short reaction sequence involving either alkylations using a dibutylstannane intermediate or by phase transfer c

Synthesis of three tethered trisaccharides to probe entropy contributions in carbohydrate-protein interactions

Crystal structure data show that the branched trisaccharide 1 constitutes the complete antigenic determinant of the Salmonella serogroup B antigen that is recognized by monoclonal antibody SE155.4. In an effort to characterize the entropic costs associated with immobilization of glycosidic torsional angles in the bound state, three distinct intramolecularly tethered analogues of this trisaccharide 2-4 have been synthesized. Two trisaccharides are tethered by a methylene acetal via the O-2 position of the 3,6-dideoxy-hexose, abequose to either O-2 of galactose (2) or O-4 of mannose (3). The third tether, α,α'-di-thio-p-xylene, spans the C-6 atoms of the mannose and galactose residues to create trisaccharide 4. The acetal tethers of 2 and 3 span hydroxyl centers that are known to be involved in intramolecular sugar-sugar hydrogens bonds, but both trisaccharides are biologically inactive due to distorted conformations that cannot be accommodated in the antibody binding site. Trisaccharide 4 is active since both hydroxymethyl groups of galactose and mannose are solvent exposed in the bound state and the constrained conformation of 4 is virtually superimposable on the bound conformation of 1. Despite the retained complimentary and significant reduction of torsional flexibility, trisaccharide 4 exhibits a ΔG° = -7.6 kcal mol-1 compared to ΔG° = -7.1 kcal mol-1 for 1. The modest free energy gain for the tethered trisaccharide 4 arises from a small entropy gain (TΔΔS = 0.3 kcal mol-1) and an even smaller enthalpic change (ΔΔH = -0.2 kcal mol-1).

REGIOSELECTIVE FORMATION OF DI-O-BENZYL-SUBSTITUTED HEXOPYRANOSIDES VIA STANNYLENE ACETAL INTERMEDIATES

The reactions of dibutylstannylene acetals derived from several methyl hexopyranosides with benzyl bromide have been investigated.These reactions occur readily in benzyl bromide at 85 deg C.At reaction times of one to two days, the major products are di-O-benzyl derivatives.In several cases, single di-O-benzyl derivatives are the predominant products: methyl α-D-glucopyranoside and methyl β-D-galactopyranoside gave the 2,6- and 3,6-di-O-benzyl ethers in 82 and 70percent yields, respectively.The species present in these reactions and the reaction pathway are discussed.

SYNTHESIS OF EVERNINOSE, A NON-REDUCING DISACCHARIDE COMPONENT OF THE ORTHOSOMYCIN-TYPE OLIGOSACCHARIDE ANTIBIOTICS

Glycosylation of 3,4-di-O-benzyl-2-O-methyl-L-lyxopyranose (1) with 3,4-di-O-benzyl-2,6-di-O-methyl-α-D-mannopyranosyl chloride afforded a mixture of the α,α- 12) and α,β-disaccharide derivative (10).Reaction of 1 with 3,4-di-O-benzyl-2,6-di-O-methyl-α-D-