73068-86-7

Basic information

• Product Name: p-tolyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside
• Synonyms: p-tolyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside
• CAS NO: 73068-86-7
• Molecular Weight: 539.379
• Mol File: 73068-86-7.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: p-tolyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: p-tolyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside(73068-86-7)
• EPA Substance Registry System: p-tolyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside(73068-86-7)

Safety Data

• Hazardous Substances Data: 73068-86-7(Hazardous Substances Data)

Upstream product

• 61198-83-2 1,2,3,4-tetra-O-benzoyl-6-desoxy-α-L-mannopyranose 
• 6155-35-7 L-rhamnose monohydrate 
• 98-88-4 benzoyl chloride 
• 3615-41-6 L-Rhamnose 
• 506-96-7 Acetyl bromide 
• 61198-83-2 1,2,3,4-tetra-O-benzoyl-α/β-L-rhamnopyranose 
• 84635-55-2 methyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 
• 115678-08-5 methyl 1-thio-α-L-rhamnopyranoside 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 115678-19-8 methyl 2,3,4-tri-O-benzoyl-1-thio-α-L-rhamnopyranoside 
• 73-34-7 L-rhamnose 

Downstream Products

• 130282-66-5 O²,O³,O⁴-Tribenzoyl-L-rhamnose 
• 80877-07-2 3,4-di-O-benzoyl-1,2-O-(alpha-methoxybenzylidene)-beta-L-rhamnopyranose 
• 76490-92-1 2,6-dichloro-2',3',4'-tri-O-benzoyl-9-α-L-rhamnopyranosylpurine 
• 77451-23-1 2,3,4-tri-O-benzoyl-1-cyano-6-deoxy-β-L-manno-hexopyranose 
• 77451-22-0 2,3,4-tri-O-benzoyl-1-cyano-6-deoxy-α-L-manno-hexopyranose 
• 161423-95-6 allyl 2-O-benzoyl-3-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-4,6-O-benzylidene-α-D-glucopyranoside 
• 31505-99-4 5-methyl-1-α-L-rhamnopyranosyl-1H-pyrimidine-2,4-dione 
• 125614-47-3 (6R)-tri-O-benzoyl-6-(2,6-bis-acetylamino-purin-9-yl)-2,6-anhydro-1-deoxy-L-mannitol 
• 101068-99-9 methyl 2,3,4-tri-O-benzoyl α-L-rhamnopyranoside 
• 161007-95-0 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate 
• 78796-87-9 2-(3',4'-di-O-benzoyl-2',6'-dideoxy-L-arabino-hex-1'-enopyranosyl)-8-amino<1,2,4>triazolo<1,5-a>pyridine 
• 78796-82-4 2-(3',4'-di-O-benzoyl-2',6'-dideoxy-L-arabino-hex-1'-enopyranosyl)-8-nitro<1,2,4>triazolo<1,5-a>pyridine 
• 78796-84-6 2-(2',3',4'-tri-O-benzoyl-6'-deoxy-α-L-manno-hexopyranosyl)-8-amino<1,2,4>triazolo<1,5-a>pyridine 
• 78796-92-6 2-(2',3',4'-tri-O-benzoyl-6'-deoxy-α-L-manno-hexopyranosyl)-6-amino<1,2,4>triazolo<1,5-a>pyridine 

Relevant articles and documents

Boronic acid-catalyzed final-stage site-selective acylation for the total syntheses of O-3′-acyl bisabolol β-D-fucopyranoside natural products and their analogues

The first concise total syntheses of O-3′-senecioyl α-bisabolol β-D-fucopyranoside (4a) and O-3′isovaleroyl α-bisabolol β-D-fucopyranoside (4b) were achieved through final-stage site-selective acylation via the activation of cis-vicinal diols by imidazole

Solasodine-3-O-β-D-glucopyranoside kills Candida albicans by disrupting the intracellular vacuole

The increasing incidence of fungal infections and emergence of drug resistance underlie the constant search for new antifungal agents and exploration of their modes of action. The present study aimed to investigate the antifungal mechanisms of solasodine-3-O-β-D-glucopyranoside (SG) isolated from the medicinal plant Solanum nigrum L. In vitro, SG displayed potent fungicidal activity against both azole-sensitive and azole-resistant Candida albicans strains in Spider medium with its MICs of 32 μg/ml. Analysis of structure and bioactivity revealed that both the glucosyl residue and NH group were required for SG activity. Quantum dot (QD) assays demonstrated that the glucosyl moiety was critical for SG uptake into Candida cells, as further confirmed by glucose rescue experiments. Measurement of the fluorescence intensity of 2′,7'-dichlorofluorescin diacetate (DCFHDA) by flow cytometry indicated that SG even at 64 μg/ml just caused a moderate increase of reactive oxygen species (ROS) generation by 58% in C. albicans cells. Observation of vacuole staining by confocal microscopy demonstrated that SG alkalized the intracellular vacuole of C. albicans and caused hyper-permeability of the vacuole membrane, resulting in cell death. These results support the potential application of SG in fighting fungal infections and reveal a novel fungicidal mechanism.

Synthesis of a chlorogenin glycoside library using an orthogonal protecting group strategy

Naturally occurring spirostanol saponins bear a chacotriose, α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→4)] -β-d-glucopyranose residue as the oligosaccharide moiety which is believed to be important for biological activity. Herein the development of a concise, combinatorial method for the synthesis of two series of glycan variants at the 2′ and/or 4′ positions of chacotriose is described and the structure-activity relationships of the glycone part at 3-OH of chlorogenin investigated. These compounds were found to be weakly-cytotoxic toward leukemia cell lines CCRF and HL-20, indicating that the chacotriose moiety is important for anticancer activity.