68027-25-8

Upstream product

• 76-83-5 trityl chloride 
• 3396-99-4 methyl α-D-galactopyranoside 
• 86172-85-2 methyl 3,6-di-O-trityl-α-D-galactopyranoside 
• 86172-84-1 (2R,3R,4S,5R,6S)-6-Methoxy-5-trityloxy-2-trityloxymethyl-tetrahydro-pyran-3,4-diol 
• 53685-07-7 Methyl 3,4-O-isopropylidene-6-O-triphenylmethyl-α-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 87591-35-3 Methyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-galactopyranoside 
• 29411-57-2 methyl-α-D-altropyranoside 

Downstream Products

• 18685-19-3 methyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-galactopyranoside 
• 38982-56-8 methyl 2,3,4-tri-O-acetyl-6-O-trityl-α-D-galactopyranoside 
• 808148-61-0 Pent-4-enoic acid (2R,3S,4S,5R,6S)-6-methoxy-4,5-bis-pent-4-enoyloxy-2-trityloxymethyl-tetrahydro-pyran-3-yl ester 
• 799269-19-5 methyl 6-O-trityl-2,3,4-tri-O-(p-toluoyl)-α-D-galactopyranoside 
• 794525-42-1 methyl 2,3,4-tri-O-(p-toluoyl)-α-D-galactopyranoside 
• 7432-72-6 Methyl 2,3,4-tri-O-acetyl-α-D-galactopyranoside 
• 76-84-6 triphenylmethyl alcohol 
• 4356-80-3 methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 
• 164323-13-1 (2S,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid 
• 83075-41-6 methyl (methyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid)uronate 
• 5155-54-4 methyl (methyl α-D-galacturonopyranoside)uronate 
• 114926-27-1 (2S,3S,4S)-1-(benzylamino)-2,3,4-tri-(benzyloxy)-5-hexene 

Relevant academic research and scientific papers

A Potent Mimetic of the Siglec-8 Ligand 6’-Sulfo-Sialyl Lewisx

Siglecs are members of the immunoglobulin gene family containing sialic acid binding N-terminal domains. Among them, Siglec-8 is expressed on various cell types of the immune system such as eosinophils, mast cells and weakly on basophils. Cross-linking of Siglec-8 with monoclonal antibodies triggers apoptosis in eosinophils and inhibits degranulation of mast cells, making Siglec-8 a promising target for the treatment of eosinophil- and mast cell-associated diseases such as asthma. The tetrasaccharide 6’-sulfo-sialyl Lewisx has been identified as a specific Siglec-8 ligand in glycan array screening. Here, we describe an extended study enlightening the pharmacophores of 6’-sulfo-sialyl Lewisx and the successful development of a high-affinity mimetic. Retaining the neuraminic acid core, the introduction of a carbocyclic mimetic of the Gal moiety and a sulfonamide substituent in the 9-position gave a 20-fold improved binding affinity. Finally, the residence time, which usually is the Achilles tendon of carbohydrate/lectin interactions, could be improved.

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.

Study of Uridine 5′-Diphosphate (UDP)-Galactopyranose Mutase Using UDP-5-Fluorogalactopyranose as a Probe: Incubation Results and Mechanistic Implications

Uridine 5′-diphosphate-5-fluorogalactopyranose (UDP-5F-Galp, 7) was synthesized, and its effect on UDP-Galp mutase (UGM) was investigated. UGM facilitated the hydrolysis of 7 to yield UDP and 5-oxogalactose (24), but no 11 was detected. 19F NMR and trapping experiments demonstrated that the reaction involves the initial formation of a substrate-cofactor adduct followed by decomposition of the resulting C5 gem-fluorohydrin to generate a 5-oxo intermediate (10). The results support the current mechanistic proposal for UGM and suggest new directions for designing mechanism-based inhibitors.

Evaluation of potential Myt1 kinase inhibitors by TR-FRET based binding assay

In the human cell cycle, the Myt1 kinase is a crucial regulator of the G2/M transition. Because this membrane-associated kinase is hard to obtain and assay, there is a distinct lack of data so far. Here we report the derivatization of a glycoglycerolipid which was shown previously to be active in a Myt1 activity assay. These compounds were tested in a binding assay together with a set of common kinase inhibitors against a full-length Myt1 expressed in a human cell line. Dasatinib exhibited nanomolar affinity whereas broad coverage inhibitors such as sunitinib and staurosporine derivatives did not show any effect. We also carried out docking studies for the most potent compounds allowing further insights into the inhibitor interaction of this kinase. The glycoglycerolipids showed no significant effects in the binding assay, endorsing the idea of a mechanism of action distant from the active site.

Highly stereoselective synthesis of primary, secondary, and tertiary α-S-sialosides under lewis acidic conditions

N-Acetyl 4-O,5-N-oxazolidinone protected sialyl phosphates of either anomeric configuration are excellent donors for the formation of α-S-sialosides at -78 °C in dichloromethane with primary, secondary, and tertiary thiols including galactose 3-, 4-, and

Efficient synthesis of (6-deoxy-glycopyranosid-6-yl) sulfone derivatives and their effect on Ca2+-ATPase

Synthesis of a series of novel (6-deoxy-glycopyranosid-6-yl) sulfone derivatives has been achieved using a general synthetic strategy. Yields were excellent in every case. The synthetic compounds were evaluated for their biological potential against Casu

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.

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.

Synthesis of D-trigalacturonic acid methylglycoside and conformational comparison with its sulfur analogue

D-Trigalacturonic acid methylglycoside (3) was synthesized to evaluate the previously synthesized sulfur analogue 1 by comparison. The NOE experiments revealed that both 3 and 1 took on a similar conformation around their glycosyl linkage.

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