95015-48-8

Upstream product

• 100-39-0 benzyl bromide 
• 14897-47-3 methyl 3,4-di-O-isopropylidene-β-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 127563-77-3 methyl 4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside 
• 194149-26-3 methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 73395-14-9 methyl (R,R)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 163125-35-7 (1'S,2'S)-Methyl 3,4-O-(1',2'-dimethoxycyclohexane-1',2'-diyl)-α-D-mannopyranoside 
• 176897-12-4 (2S,3S,4aR,5R,7S,8S,8aR)-5-(hydroxymethyl)-2,3,7-trimethoxy-2,3-dimethylhexahydro-2Hpyrano[3,4-b][1,4]dioxin-8-ol4 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 195192-32-6 (2'S,3'S)-Methyl 2,6-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-mannopyranoside 
• 163125-46-0 (1'S,2'S)-Methyl 2,6-di-O-benzyl-3,4-O-(1',2'-dimethoxycyclohexane-1',2'-diyl)-α-D-mannopyranoside 
• 87976-40-7 methyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 4148-71-4 methyl (exo-Ph)-2,3: 4,6-di-O-benzylidene-α-D-mannopyranoside 

Downstream Products

• 109681-27-8 (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-((2R,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yloxy)-3-hydroxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 109681-26-7 (2S,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-((2R,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yloxy)-3-hydroxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl α-D-galactopyranoside 
• 51842-16-1 methyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside 
• 55697-53-5 methyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 127563-77-3 methyl 4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside 
• 286860-87-5 (1(1')-Z)-2,3,4,6-tetra-O-benzyl-1-deoxy-1-(ethoxysulfonyl)methylidene-D-glucopyranose 
• 223582-39-6 methyl 2,6-di-O-benzyl-3-O-(3,4,5,7-tetra-O-benzyl-1-deoxy-1-ethylsulfonato-α-D-gluco-hept-2-ulopyranosyl)-β-D-galactopyranoside 
• 1057490-76-2 C₄₂H₅₁NO₂₀ 
• 934592-21-9 methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside 
• 1173284-93-9 methyl 5-acetamido-4,7,8,9-tetra-O-benzoyl-5-N-benzoyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

Experimental and theoretical study of the O3/O4 regioselectivity of glycosylation reactions of glucopyranosyl acceptors

The knowledge of the regioselectivity between different hydroxyl groups of glycosyl acceptors is valuable in planning simple strategies for the synthesis of oligosaccharides, minimizing the use of protecting groups. With the aim of obtaining deeper knowle

Regioselectivity of glycosylation reactions of galactose acceptors: An experimental and theoretical study

Regioselective glycosylations allow planning simpler strategies for the synthesis of oligosaccharides, and thus reducing the need of using protecting groups. With the idea of gaining further understanding of such regioselectivity, we analyzed the relative

A novel O-fucosylation strategy preactivated by (p-Tol)2SO/Tf2O and its application for the synthesis of Lewis blood group antigen Lewisa

Based on a preactivation strategy using (p-Tol)2SO/Tf2O, a new O-fucosylation method with thioglycoside as donor under mild conditions was reported. High yields and excellent α-stereoselectivities of the fucosylation were obtained wi

A green and convenient method for regioselective mono and multiple benzoylation of diols and polyols

An efficient method for regioselective benzoylation of diols and polyols was developed. The benzoylation is catalyzed by only 0.2 equiv of benzoate anion in acetonitrile with the addition of a stoichiometric amount of benzoic anhydride under very mild condition, leading to high yields. Compared with all other methods, this method shows particular advantage in regioselective multiple benzoylation of polyols, and in avoiding the use of any metal-based catalysts and any amine bases, which is more environment-friendly.

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

Rapid assembly of gp120 oligosaccharide moieties via one-pot glycosidation-deprotection sequences

Mannosyl trihaloacetimidate donors equipped with a 2-O-Fmoc group can be effectively activated by catalytic Bi(OTf)3 in glycosidations. Despite the expected participating effect of the Fmoc group, the reaction solvent was found to be decisive f

Reductive openings of benzylidene acetals revisited: A mechanistic scheme for regio- and stereoselectivity

Despite the importance of regioselective reductive openings of cyclic acetals, mechanistic details are scarce. In this study 4,6-O-benzylidene acetals were used as model compounds for deciphering the mechanism of regioselective openings using a variety of

FeCl3-catalysed cleavage of 1,2-butanediacetal protected diols

Catalytic FeCl3 in acetic acid has been employed as a cost-effective, low-toxicity reagent for the removal of butane 1,2-diacetal protecting groups under mild conditions. Georg Thieme Verlag Stuttgart.

Carbohydrate Phosphinites as Practical Ligands in Asymmetric Catalysis: Electronic Effects and Dependence of Backbone Chirality in Rh-Catalyzed Asymmetric Hydrogenations. Synthesis of R- or S-Amino Acids Using Natural Sugars as Ligand Precursors

Vicinal diarylphosphinites derived from carbohydrates are excellent ligands for the Rh(I)-catalyzed enantioselective asymmetric hydrogenation of dehydroamino acid derivatives, producing the highest enantioselectivity of any ligands directly prepared from natural products. The enantioselectivity can be enhanced by the appropriate choice of substituents on the aromatic rings of the phosphinites. For example, the use of phosphinites with electron-donating bis(3,5-dimethylphenyl) groups on phosphorus provides ee's up to 99% for a wide range of amino acids including some with easily removable N-protecting groups. Electron-withdrawing aryl substituents, on the other hand, decrease the enantioselectivity. Sense of chiral induction in the amino acid product depends on the relative juxtaposition of the vicinal diphosphinites on a given sugar backbone. When readily available D-glucopyranosides are used as the starting sugars, 2,3-phosphinites give the S-amino acids and 3,4-phosphinites give the R-amino acids. In the case of aromatic and heteroaromatic amino acids, enantioselectivities > 95% are consistently obtained. Practical considerations such as the ease of ligand synthesis, rates of reactions, catalyst turnover, and scope and limitations in terms of substrates are discussed. A possible explanation for the enhancement of enantioselectivity by electron-rich phosphinites is offered.

Direct preparation of diacetals from 1,2-diketones and their use as 1,2-diol protecting groups

A range of 1,2-diketones have been evaluated as potential protecting groups for trans-1,2-diols via 1,2-diacetal formation. The procedure is especially useful in oligosaccharide and natural product synthesis.