134149-34-1

Upstream product

• 532-20-7 L-arabinose 
• 107-18-6 allyl alcohol 
• 532-20-7 D-Ribose 
• 50-69-1 D-ribose 
• 106-95-6 allyl bromide 
• 22796-65-2 p-nitrophenyl α-L-arabinofuranoside 
• 404574-12-5 methyl 2,3,5-tri-O-benzoyl-1-α-L-arabinofuranoside 
• 5328-37-0 L-arabinose 
• 58-86-6 D-xylose 
• 13039-64-0 (2S,3R,4R)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3,4-diol 
• 100645-43-0 p-nitrophenyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranoside 
• 189074-35-9 1-O-Acetyl-2,3,5-tri-O-benzoyl-α/β-L-arabinofuranoside 

Downstream Products

• 121682-55-1 allyl-2,3,5-tri-O-benzyl-α,β-L-arabinofuranoside 
• 251451-10-2 allyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-α-L-arabinofuranoside 
• 251451-16-8 C₆₅H₆₂Cl₃NO₂₆ 
• 251451-18-0 C₆₆H₆₆O₂₆ 
• 934822-33-0 allyl 3-nitro-3-deoxy-6-O-tosyl-β-D-glucopyranoside 
• 134149-36-3 prop-1-enyl 2,3,5-tri-O-benzyl-α,β-L-arabinofuranoside 
• 89615-42-9 2,3,5-tri-O-benzyl-β-L-arabinofuranose 
• 251451-14-6 allyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyl-(1->5)-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-L-arabinofuranoside 
• 251451-11-3 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyl trichloroacetimidate 
• 313468-65-4 allyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranoside 
• 313468-67-6 allyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzyl-α-L-arabinofuranoside 
• 251451-12-4 (2R,3R,4R,5S)-2-((2S,3S,4R,5R)-5-Allyloxy-3,4-bis-benzyloxy-tetrahydro-furan-2-ylmethoxy)-5-hydroxymethyl-tetrahydro-furan-3,4-diol 

Relevant academic research and scientific papers

Araf51 with improved transglycosylation activities: One engineered biocatalyst for one specific acceptor

A random mutagenesis of the arabinofuranosyl hydrolase Araf51 has been run in order to have access to efficient biocatalysts for the synthesis of alkyl arabinofuranosides. The mutants were selected on their ability to catalyze the transglycosylation reaction of p-nitrophenyl α-l-arabinofuranoside (pNP-Araf) used as a donor and various aliphatic alcohols as acceptors. This screening strategy underlined 5 interesting clones, each one corresponding to one acceptor. They appeared to be much more efficient in the transglycosylation reaction compared to the wild type enzyme whereas no self-condensation or hydrolysis products could be detected. Moreover, the high specificity of the mutants toward the alcohols for which they have been selected validates the screening process. Sequence analysis of the mutated enzymes revealed that, despite their location far from the active site, the mutations affect significantly the kinetics properties as well as the substrate affinity of these mutants toward the alcohol acceptors in the transglycosylation reaction.

Anomeric alkylations and acylations of unprotected mono- and disaccharides mediated by pyridoneimine in aqueous solutions

A site-specific deprotonation followed by alkylations and acylations of sugar hemiacetals to the corresponding alkyl glycosides and acylated sugars in aqueous solutions is disclosed herein. Pyridoneimine as a new base is developed to mediate the deprotonation of readily available sugar hemiacetals and further reactions with alkylation and acylation agents.

Analysis of Configuration and Conformation of Furanose Ring in Carbohydrate and Nucleoside by Vibrational Circular Dichroism

A reliable and convenient method for determining the configuration and conformation of the furanose ring in carbohydrates and nucleosides by vibrational circular dichroism (VCD) spectroscopy is described. Diastereomeric pairs of several furanose monosacch

Sulfonated graphene oxide as highly efficient catalyst for glycosylation

Heterogeneous sulfonated graphene oxide for the first time has been used as a green and efficient catalyst for atom-economic glycosylation of unprotected, unactivated glycosyl donors or 2,3,4,6-tetra-O-acetylglycosyltrichloroacetimidate with various accep

Synthesis of the spirastrellolide A, B/C spiroketal: Enabling solutions for problematic au(I)-catalyzed spiroketalizations

A synthesis of the spirastrellolide A, B/C-ring monounsaturated spiroketal is reported. The key step relies on a Au-catalyzed spiroketalization of a propargyl triol employing an acetonide as a regioselectivity regulator. Through observation and analysis, a set of conditions has been developed that facilitates the use of a mixture of diastereomeric substrates, obviating the need to control the stereochemistry of the propargyl stereocenter and enabling a convenient retrosynthetic disconnection. The key reaction proceeds in 80% yield in 1 min at ambient temperature with the Me3PAuCl/AgOTf catalyst system. These conditions should be widely applicable for new synthetic endeavors as they appear to overcome all issues with the Au-catalyzed spiroketalization.

Araf51 with improved transglycosylation activities: One engineered biocatalyst for one specific acceptor

A random mutagenesis of the arabinofuranosyl hydrolase Araf51 has been run in order to have access to efficient biocatalysts for the synthesis of alkyl arabinofuranosides. The mutants were selected on their ability to catalyze the transglycosylation reaction of p-nitrophenyl α-l-arabinofuranoside (pNP-Araf) used as a donor and various aliphatic alcohols as acceptors. This screening strategy underlined 5 interesting clones, each one corresponding to one acceptor. They appeared to be much more efficient in the transglycosylation reaction compared to the wild type enzyme whereas no self-condensation or hydrolysis products could be detected. Moreover, the high specificity of the mutants toward the alcohols for which they have been selected validates the screening process. Sequence analysis of the mutated enzymes revealed that, despite their location far from the active site, the mutations affect significantly the kinetics properties as well as the substrate affinity of these mutants toward the alcohol acceptors in the transglycosylation reaction.

Direct glycosylation of unprotected and unactivated carbohydrates under mild conditions

Ligand exchange acetalization of acetals in the presence of catalytic amounts of mandelic acid and titanium tert-butoxide is reported. This transformation is successfully extended to glycosylation of unprotected and unactivated pentoses. Even unreactive pentoses such as d-arabinose or d-lyxose can be transformed by this new methodology into corresponding isopropyl glycosides.

Green glycosylation promoted by reusable biomass carbonaceous solid acid: An easy access to β-stereoselective terpene galactosides

An efficient green protocol has been developed for the atom economic glycosylation of unprotected, unactivated glycosyl donors and glycosylation of glycosyl trichloroacetimidates with the aid of reusable eco-friendly biomass carbonaceous solid acid as catalyst. The Royal Society of Chemistry.

Synthesis of congeners of migrastatin and dorrigocin A from d-xylose

Migrastatin and dorrigocin A analogues have potential as anti-metastatic agents that act by targeting the actin-bundling protein, fascin. Syntheses of close structural analogues of these agents have been achieved. Wittig and Ando olefination reactions with an aldehyde obtained from d-xylose, respectively, gave two trisubstituted alkene intermediates that were then elaborated into either macrolactone or macrolactam analogues of migrastatin or to an acyclic dorrigocin A analogue.

Carbohydrate mimic of 2-deoxystreptamine for the preparation of conformationally constrained aminoglycosides

The synthesis of a carbohydrate mimic of 2-deoxystreptamine (2-DOS) is described starting from d-ribose. Crucial steps of the synthesis involve a stereoselective nitroaldol condensation and deoxygenation via elimination-in situ reduction. Moreover, glycos