594841-23-3

Upstream product

• 63734-12-3 methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 74247-81-7 6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 3396-99-4 methyl α-D-galactopyranoside 
• 181480-80-8 6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 74247-82-8 Methyl 6-O-<(1,1-dimethylethyl)dimethylsilyl>-β-D-galactopyranoside 
• 141-78-6 ethyl acetate 

Downstream Products

• 71512-68-0 methyl 1,2,4-tri-O-acetyl-6-O-benzyl-α-D-glucopyranoside 
• 81348-21-2 methyl 2,3,4-tri-O-acetyl-6-O-benzyl-α-D-galactopyranoside 
• 7432-72-6 Methyl 2,3,4-tri-O-acetyl-α-D-galactopyranoside 
• 7432-72-6 methyl 2,3,4-tri-O-acetyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

ZWITTERIONIC CATALYSTS FOR (TRANS)ESTERIFICATION: APPLICATION IN FLUOROINDOLE-DERIVATIVES AND BIODIESEL SYNTHESIS

An amide/iminium zwitterion catalyst has a catalyst pocket size that promotes transesterification and dehydrative esterification. The amide/iminium zwitterions are easily prepared by reacting aziridines with aminopyridines. The reaction can be applied a wide variety of esterification processes including the large-scale synthesis of biodiesel. The amide/iminium zwitterions allow the avoidance of strongly basic or acidic condition and avoidance of metal contamination in the products. Reactions are carried out at ambient or only modestly elevated temperatures. The amide/iminium zwitterion catalyst is easily recycled and reactions proceed in high to quantitative yields.

Amide/Iminium Zwitterionic Catalysts for (Trans)esterification: Application in Biodiesel Synthesis

A class of zwitterionic organocatalysts based on an amide anion/iminium cation charge pair has been developed. The zwitterions are easily prepared by reacting aziridines with aminopyridines. They are catalytically applicable to transesterifications and dehydrative esterifications. Mechanistic studies reveal that the amide anion and iminium cation work synergistically in activating the reaction partners, with the iminium cationic moiety interacting with the carbonyl substrates through nonclassical hydrogen bonding. The reaction can be applied to large-scale synthesis of biodiesel under mild conditions.

Ceric ammonium nitrate/acetic anhydride: A tunable system for the O-acetylation and mononitration of diversely protected carbohydrates

Esterification of a wide range of partially protected carbohydrate derivatives was achieved using acetic anhydride and a catalytic amount of ceric ammonium nitrate (CAN). Compatibility with the commonly used protecting groups was demonstrated, with the es

Crystal structure analysis of 2,3,4-Tri-O-acetyl-α-methyl-D-glucopyranoside

2,3,4-Tri-O-acetyl-α-methyl-D-glucopyranoside (F.W. 319.28) was synthesized, characterized by 1H NMR, confirmed by X-ray crystal structure analysis. This compound crystallizes in monoclinic class under the space group orthorhombic P2(1)2(1)2(1) with cell parameters a = 9.0312(18) A?, b = 11.731(2) A?, c = 15.139(3) A?; Z = 4. The structure exhibits inter-molecular hydrogen bonds of the type O-H - O, C-H - O.

DABCO: An efficient promoter for the acetylation of carbohydrates and other substances under solvent-free conditions

A simple, mild and efficient solvent-free method for the acetylation of carbohydrates, and their partially protected derivatives, as well as non-carbohydrate substances in excellent yields in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) is described with the advantage of tolerance to various functional groups, short reaction time and ease of product isolation.

Fe2(SO4)3·xH2O-catalyzed per-O-acetylation of sugars compatible with acid-labile protecting groups adopted in carbohydrate chemistry

Fully acetylated saccharides are inexpensive and very useful starting materials for the synthesis of many naturally occurring glycosides, oligosaccharides, and glycoconjugates. Ferric sulfate hydrate (Fe2(SO4)3·xH2O) was found to be a valuable Lewis acid promoter in the per-O-acetylation reaction of saccharides with acetic anhydride in 100% of conversion rate and 88-99% yields. Interestingly, the procedure is perfectly compatible with the presence of a variety of acid-labile protecting groups, such as isopropylidene, benzylidene, trityl, and TBDMS groups. The reactions were simply performed by stirring the mixture of a sugar with a slight excessive acetic anhydride in the presence of 2.0 mol % of Fe2(SO4)3·xH2O at rt and the pure products were obtained by a simple dilution of the reaction mixture with dichloromethane and washings with aqueous Na2CO3.

Synthesis of S-linked carbohydrate analogues via a Ferrier reaction

In this work, the synthetic utility of the Ferrier reaction to access S-linked disaccharides and S-linked glycoamino acids has been probed. Significantly, entry to a range of 1,4- and 1,6-S-linked disaccharides has been achieved using glycals derived from glucose and galactose, and sulfur containing coupling partners derived from methyl α-d-glucopyranoside. Access to S-linked glycoamino acids and glycopeptides has also been achieved using protected cysteine and homocysteine coupling partners within the Ferrier reaction. Functionalisation of the Ferrier products, for example, via dihydroxylation using OsO4 or amino acid coupling, and deprotection of the targets have also been achieved. In this way, entry to materials of interest as mimics of biologically interesting disaccharides and glycopeptides has been realised, including targets derived from rare sugars such as talopyranose and gulopyranose.

Application of ball milling technology to carbohydrate reactions: I. Regioselective primary hydroxyl protection of hexosides and nucleoside by planetary ball milling

Dry ball milling of hexosides with trityl chloride in the presence of DABCO or Na2CO3 has been found to result in their complete conversion to the respective 6-O-trityl ethers. Further wet grinding of the reaction mixture with Ac2O in the presence of DMAP led to the respective fully protected hexosides in good to excellent yields after isolation. It has been found to be an effective one-pot two-step synthesis under solvent-free condition. The speed of homogenization has been shown to highly influence the rate and outcome of the reaction, and commercially available planetary ball mill has been proved to be very convenient for carrying out the reaction under standardized and reproducible conditions.

A facile, one-step conversion of 6-O-trityl and 6-O-TBDMS monosaccharides into the corresponding formate esters

A convenient method has been developed for a facile and high-yield conversion of 6-O-tert-butyldimethylsilyl and 6-O-trityl protected monosaccharides to their formate esters, which may serve as useful intermediates for the replacement of the primary hydro