18031-49-7

Usage

Type

Organic compound

Derivative

Sugar glucose

Substituents

Methyl group attached to the 6th carbon
Three acetyl groups attached to hydroxyl groups
Triphenylmethyl group serving as a protecting group

Purpose of Triphenylmethyl Group

Preventing unwanted reactions at the hydroxyl group

Applications

Used in organic synthesis
Particularly useful in synthesizing complex carbohydrates and bioactive molecules

Importance

Crucial for pharmaceutical production
Vital in the synthesis of natural products and other organic compounds

InChI:InChI=1/C32H34O9/c1-21(33)38-28-27(41-31(36-4)30(40-23(3)35)29(28)39-22(2)34)20-37-32(24-14-8-5-9-15-24,25-16-10-6-11-17-25)26-18-12-7-13-19-26/h5-19,27-31H,20H2,1-4H3

Upstream product

• 108-24-7 acetic anhydride 
• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 
• 76-83-5 trityl chloride 
• 29411-57-2 methyl-α-D-altropyranoside 
• 604-70-6 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 3458-28-4 D-Mannose 
• 20231-36-1 methyl 6-O-trityl-α-D-mannopyranoside 
• 596-43-0 bromo-triphenyl-methane 

Downstream Products

• 6639-43-6 2,2,2-triphenylacetonitrile 
• 76951-67-2 methyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 7432-72-6 methyl 2,3,4-tri-O-acetyl-α-D-mannopyranoside 
• 1372204-42-6 methyl 6-deoxy-6-(4-(5-trifluoromethyl-2(1H)-pyridone-1-yl)-anilino)-α-D-mannopyranoside 
• 1372204-43-7 methyl 6-deoxy-6-(3-chloro-4-(5-trifluoromethyl-2(1H)-pyridone-1-yl)-anilino)-α-D-mannopyranoside 
• 1372204-44-8 methyl 6-deoxy-6-(3-(5-trifluoromethyl-2(1H)-pyridone-1-yl-methyl)-anilino)-α-D-mannopyranoside 
• 6087-46-3 methyl 2,3,4-tri-O-acetyl-6-chloro-6-deoxy-α-D-glucopyranoside 
• 130052-62-9 methyl-2,3,4-tri-O-acetyl-6-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 1372204-41-5 methyl 6-deoxy-6-(2-(5-trifluoromethyl-2(1H)-pyridone-1-yl-methyl)-anilino)-α-D-glucopyranoside 

Relevant academic research and scientific papers

Visible-Light-Mediated, Chemo- and Stereoselective Radical Process for the Synthesis of C-Glycoamino Acids

An approach for efficient synthesis of C-glycosyl amino acids is described. Different from typical photoredox-catalyzed reactions of imines, the new process follows a pathway in which α-imino esters serve as electrophiles in chemoselective addition reactions with nucleophilic glycosyl radicals. The process is highlighted by the mild nature of the reaction conditions, the highly stereoselectivity attending C-C bond formation, and its applicability to C-glycosylations using both armed and disarmed pentose and hexose derivatives.

MACROCYCLIC MCL-1 INHIBITORS AND METHODS OF USE

The present disclosure provides for compounds of Formula (I) wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of Formula (I).

Diazepinium perchlorate: a neutral catalyst for mild, solvent-free acetylation of carbohydrates and other substances

Diazepinium perchlorate, an essentially neutral organic salt possessing excellent stability, has been found to be well suited for the acetylation of free as well as partially protected sugars, phenols, thiophenols, thiols and other alcohols as well as amines. The diazepinium perchlorate-catalyzed acetylation is mild, organic and solvent-free and leaves acid sensitive protecting groups such as TBDMS/TBDPS/Tr ethers and isopropylidene/benzylidene acetals present on a substrate unaffected. Regioselective hydroxyl protection in partially protected carbohydrate derivatives/polyhydroxylic compounds was possible and was proved to be a convenient time-saving alternative to the conventional synthesis of such compounds. Easy preparation of the catalyst, mild reaction conditions and an environmentally benign protocol are some of the notable features of this reaction. The results obtained on the acetylation of phenols and thiophenols could be rationalized through their local nucleophilicity index obtained from DFT calculations.

Acyl transfer reactions of carbohydrates, alcohols, phenols, thiols and thiophenols under green reaction conditions

Acyl transfer reactions of various carbohydrates, alcohols, phenols, thiols and thiophenols were achieved at room temperature in high yields and catalytic efficiency in the presence of methane sulfonic acid, a green organic acid, under solvent-free conditions over short time periods. The method is mild enough to allow acid labile substituents such as isopropylidene acetals and trityl ethers on the reacting substrates to be left completely unaffected. Esterification of free mono- and dicarboxylic acids such as acetic acid, cinnamic acid, sialic acid and tartaric acid with alcohols such as menthol, ethanol, methanol or propylene glycol has also been achieved efficiently at room temperature. A comparative study of the method with the silica-sulfuric acid is also reported.

Design, synthesis and antifibrotic activities of carbohydrate-modified 1-(substituted aryl)-5-trifluoromethyl-2(1H) pyridones

Pirfenidone, a pyridone compound, is an effective and novel antifibrotic agent. In this article, we describe the design, synthesis and activity evaluation of novel antifibrotic agents, 1-(substituted aryl)-5-trifluoromethyl- 2(1H) pyridones modified with

Synthesis of a Candida albicans tetrasaccharide spanning the β1,2-mannan phosphodiester α-mannan junction

The cell wall phosphomannan of Candida species is a complex N-linked glycoprotein with a glycan chain containing predominantly an α-linked mannose backbone with α-mannose branches. A minor β-mannan component is attached to the branches either via a glycos

Design, synthesis, and biological evaluation of novel carbohydrate-based sulfamates as carbonic anhydrase inhibitors

Carbonic anhydrases (CAs) IX and XII are enzymes with newly validated potential for the development of personalized, first-in-class cancer chemotherapies. Here we present the design and synthesis of novel carbohydrate-based CA inhibitors, several of which were very efficient inhibitors (Ki10 nM) with good selectivity for cancer-associated CA isozymes over off-target CA isozymes. All inhibitors comprised a carbohydrate core with one hydroxyl group derivatized as a sulfamate. Five different carbohydrates were chosen to present a selection of molecular shapes with subtle stereochemical differences to the CA enzymes active site. Variable modifications of the remaining sugar hydroxyl groups were incorporated to provide an incremental coverage of chemical property parameters that are associated with biopharmaceutical performance. All sulfamate inhibitors displayed ligand efficiencies that are consistent with those reported for good drug lead candidates.

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.

Novel selectivity in carbohydrate reactions, IV: DABCO-mediated regioselective primary hydroxyl protection of carbohydrates

An efficient procedure for the regioselective tritylation of primary hydroxyl group of aldohexopyranosides and nucleosides using trityl chloride in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) in dichloromethane has been developed. Subsequent acetylation of the tritylated products in the same pot has been made possible, thereby providing an efficient route to the fully protected carbohydrate derivatives that can be discriminated chemoselectively.

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.