620951-70-4

Upstream product

• 106-45-6 para-thiocresol 
• 30021-94-4 1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 
• 793696-64-7 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl iodide 
• 73-34-7 L-rhamnose 
• 108-24-7 acetic anhydride 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 103-19-5 di(p-tolyl) disulfide 
• 5158-64-5 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide 

Downstream Products

• 628308-75-8 (2S,3S,4R,5R,6S)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyranol 
• 1111726-58-9 propargyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-3-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 791836-43-6 para-tolyl 2-O-allyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 
• 791836-35-6 (2'S,3'S)-para-tolyl 2-O-allyl-3,4-O-(2',3'-dimethoxybutan-2',3'-diyl)-1-thio-α-L-rhamnopyranoside 
• 791836-34-5 (2'S,3'S)-para-tolyl 3,4-O-(2',3'-dimethoxybutan-2',3'-diyl)-1-thio-α-L-rhamnopyranoside 
• 791836-41-4 para-tolyl 2-O-allyl-1-thio-α-L-rhamnopyranoside 
• 916994-68-8 2,3,4-O-tribenzyl-1-(4-tolyl)thio-α-L-rhamnopyranoside 
• 83866-10-8 (2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate 
• 210426-02-1 2,3,4-tri-O-benzyl-L-rhamnopyranose 
• 944153-63-3 2,3,4-O-tribenzyl-α-L-rhamnosyl(1->3)-4-O-acetyl-2-O-benzoyl-1-O-trichloroacetimido-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

Synthesis of disaccharide modified berberine derivatives and their anti-diabetic investigation in zebrafish using a fluorescence-based technology

Berberine is a naturally occurring isoquinoline alkaloid and has been used as an important functional food additive in China due to its various pharmacological activities. Berberine exhibits great potential for developing anti-diabetic agents against type

SYNTHETIC LIPOPEPTIDE VACCINES AND IMMUNOTHERAPEUTICS

Single molecules useful in vaccine compositions, and methods of making and using the same, are described.

Synthesis of α-l-rhamnosyl ceramide and evaluation of its binding with anti-rhamnose antibodies

An α-l-rhamnosyl ceramide (1, α-l-RhaCer) has been prepared that was recognized by anti-l-rhamnose (anti-Rha) antibodies. During these studies we explored the use of an α-l-rhamnosyl thioglycoside and a trichloroacetimidate as a glycosyl donors. Subsequently, the acceptors desired for glycosylation, 3-O-benzoylazidosphingosine or 3-O-alloxycarbonylsphingosine, were prepared from d-xylose. The thioglycoside donor, 2,3,4-tri-O-acetyl-1-(4-tolyl)thio-α-l-rhamnopyranoside, and the trichloroacetimidate donor, 2,3,4-tri-O-acetyl-1-(2,2,2-trichloroethanimidate)-α-l-rhamnopyranoside, were synthesized in 50% and 78% yield overall, respectively. The synthesis of the glycosylation acceptor employed an addition-fragmentation olefination that was successfully carried out in 53% yield. With the successful synthesis of key intermediates, α-l-RhaCer (1) was prepared without any insurmountable obstacles. Anti-Rha antibodies were prepared in BALB/c mice by immunizing them with rhamnose-ovalbumin (Rha-Ova) with Sigma Adjuvant System (SAS) and the anti-l-Rha antibodies were isolated from the blood sera. Liposomes and EL4 tumor cells were used as model systems to demonstrate the ability of 1 to insert into a lipid bilayer. The interaction of the liposomes or the EL4 cells with α-l-RhaCer (1) and anti-Rha antibodies were investigated by fluorescence microscopy and flow cytometry, respectively, to confirm the ability of glycolipid 1 to be displayed on the tumor cell surface as well as the ability to be recognized by anti-Rha antibodies.

A facile and efficient method for the one-pot synthesis of per-O-acetylated thioglycosides from unprotected sugars

An efficient, convenient protocol for the preparation of per-O-acetylated p-tolylthio glycosides is described. Treatment of various unprotected sugars, including 2-deoxy-2-amino sugars, sialic acid, lactose, and maltose, with acetic anhydride using SnCl4 as a catalyst, and subsequently with p-tolylthiol, furnished the corresponding thioglycosides in 71%-90% yield under solvent-free conditions.

Synthesis of thioglycosides in room temperature ionic liquid

An eco-friendly reaction for the preparation of thioglycosides has been developed using an ionic liquid as the solvent. Thioglycosides were obtained in excellent yields on treatment of per-O-acetylated sugar derivatives with thiols in the presence of boro

Odorless eco-friendly synthesis of thio- and selenoglycosides in ionic liquid

An environmentally benign odorless methodology for the preparation of 1,2-trans-thio- and selenoglycosides is reported. In a one-pot condition, the reductive cleavage of disulfides and diselenides using triethylsilane and borontrifluoride diethyletherate combination followed by the reaction of the in situ generated thiolate and selenoetes with glycosyl acetate derivatives in recyclable room-temperature ionic liquid, [BMIM]BFresulted in excellent yields of thio- and selenoglycosides avoiding the use of obnoxious thiols/selenols and metallic catalysts.

Synthesis of the rhamnosyl trisaccharide repeating unit to mimic the antigen determinant of Pseudomonas syringae lipopolysaccharide

The trisaccharide 2,3,4-O-tribenzyl-α-L-rhamnosyl-(1→3)-4-O- acetyl-2-O-benzoyl-(1→2)-4-O-acetyl-3-O-benzoyl-α-L-rhamnosyl-1-(4- tolyl)thio-α-L-rhamnopyranoside was prepared from the thio-sugar 1-(4-tolyl)thio-α,β-L-rhamnopyranoside from the nonreducing e

Lanthanum trifluoromethane-sulfonate-catalyzed facile synthesis of per-O-acetylated sugars and their one-pot conversion to S-aryl and O-alkyl/aryl glycosides

Lanthanum trifluoromethanesulfonate-catalyzed solvent-free per-O-acetylation with stoichiometric acetic anhydride proceeds in high yield (95%-99%) to afford exclusively pyranose products as anomeric mixtures. Subsequent anomeric substitution employing borontrifluoride etherate and thiols or alcohols furnished the corresponding 1,2-trans-linked thioglycosides and O-glycosides, respectively, in good to excellent overall yield (75%-85%). Alternatively, reaction of free sugars in neat alcohol employing the same catalyst at elevated temperature gives the corresponding 1,2-cis-linked O-glycosides (along with 1,2-trans-linked glycosides as minor product) in good yield (73%-80%). Anomeric mixtures of compounds thus produced were characterized as their per-O-acetylated derivatives.

Synthesis of thio- and selenoglycosides by cleavage of dichalconides in the presence of zinc/zinc chloride and reaction with glycosyl bromides

A convenient odorless methodology has been devised for the preparation of 1,2-trans-thio- and selenoglycosides through zinc-mediated cleavage of disulfides and diselenides and reaction of the thiolate and selenides formed in situ with glycosyl bromides. T

A generalized procedure for the one-pot preparation of glycosyl azides and thioglycosides directly from unprotected reducing sugars under phase-transfer reaction conditions

Per-O-acetylated glycosyl azides and thioglycosides were prepared in excellent yield directly from unprotected reducing sugars through in situ generation of per-O-acetylated glycosyl bromides by a generalized one-pot procedure under phase-transfer conditions. Stereoselective products were formed with complete inversion at the anomeric centers of the glycosyl bromides to provide a general high-yielding procedure for the preparation of 1,2-trans-glycosyl azides and thioglycosides. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.