620951-70-4

Basic information

• Product Name: p-tolyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside
• Synonyms: p-tolyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside
• CAS NO: 620951-70-4
• Molecular Weight: 396.461
• Mol File: 620951-70-4.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: p-tolyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: p-tolyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside(620951-70-4)
• EPA Substance Registry System: p-tolyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside(620951-70-4)

Safety Data

• Hazardous Substances Data: 620951-70-4(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 944153-61-1 2,3,4-O-tribenzyl-α-L-rhamnosyl(1->3)-4-O-acetyl-2-O-benzoyl-1-(4-tolyl)thio-α-L-rhamnopyranoside 
• 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 
• 210426-02-1 2,3,4-tri-O-benzyl-L-rhamnopyranose 
• 83866-10-8 (2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate 
• 916994-68-8 2,3,4-O-tribenzyl-1-(4-tolyl)thio-α-L-rhamnopyranoside 

Relevant articles and documents

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

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.

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