3891-58-5

Usage

InChI:InChI=1/C13H18O9/c1-7(15)19-6-12(21-9(3)17)13(22-10(4)18)11(5-14)20-8(2)16/h5,11-13H,6H2,1-4H3

Upstream product

• 58-86-6 D-xylose 
• 108-24-7 acetic anhydride 
• 59-23-4 D-Galactose 
• 7226-49-5 2,3,4,5-tetra-O-acetyl-D-xylose diethyl dithioacetal 

Downstream Products

• 86334-50-1 1-deoxy-D-gulitol 
• 120401-38-9 2,3,4,5-tetra-O-acetyl-D-arabinose benzoylhydrazone 
• 404344-58-7 (2R,3R)-3-(1',2',3',4'-tetra-O-acetyl-D-arabino-tetritol-1'-yl)-2-[4-benzyl-2-(4-methoxyphenyl)-1,3-dioxo-2,4-diazapentyl]-2-phenylthiirane 
• 404344-61-2 (2S,3S)-3-(1',2',3',4'-tetra-O-acetyl-D-arabino-tetritol-1'-yl)-2-[4-benzyl-2-(4-methoxyphenyl)-1,3-dioxo-2,4-diazapentyl]-2-phenylthiirane 
• 5328-63-2 methyl-β-D-arabinopyranoside 
• 4594-60-9 methyl 3,4-O-isopropylidene-β-D-arabinopyranoside 
• 869848-87-3 Acetic acid (2S,3S,4R,5R)-4,5-diacetoxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester 
• 6632-52-6 tetra-O-acetyl-keto-1-deoxy-DL-fructose 
• 57-48-7 D-Fructose 
• 3615-56-3 D-Sorbose 
• 7208-41-5 penta-O-acetyl-6-deoxy-L-glucitol 
• 7208-41-5 penta-O-acetyl-1-deoxy-D-iditol 
• 172886-59-8 2,4,6-Trimethyl-benzenesulfonic acid (R)-2-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-2-hydroxy-ethyl ester 

Relevant academic research and scientific papers

Indiosides G-K: Steroidal glycosides with cytotoxic and anti-inflammatory activities from Solanum violaceum

Five new steroidal glycosides (1-5) and nine known compounds were isolated from Solanum violaceum. Indiosides G (1) and H (2) are spirostene saponins with an iso-type F ring, indioside I (3) is a spirostane saponin, and indiosides J (4) and K (5) are unusual furostanol saponins with a deformed F ring. These structures represent rare naturally occurring steroidal skeletons. The structures of the new compounds were elucidated using 1D and 2D spectroscopic techniques and acid hydrolysis. Compounds 2, 3, and 7-9 exhibited cytotoxic activity against six human cancer cell lines (HepG2, Hep3B, A549, Ca9-22, MDA-MB-231, and MCF-7) with IC50 values of 1.83-8.04 μg/mL. Steroidal saponins 3, 8, and 9 showed inhibitory effects on superoxide anion generation with IC50 values of 2.84 ± 0.18, 0.62 ± 0.03, and 1.62 ± 0.59 μg/mL, respectively. Saponins 8 and 9 also inhibited elastase release with IC50 values of 111.05 ± 7.37 and 4.04 ± 0.51 μg/mL, respectively. Structure-activity relationship correlations of these compounds with respect to cytotoxic and anti-inflammatory effects are discussed.

Tandem epoxidation-alcoholysis or epoxidation-hydrolysis of glycals catalyzed by titanium(IV) isopropoxide or Venturello's phosphotungstate complex

Venturello's phosphotungstate complex and titanium(IV) isopropoxide [Ti(O-i-Pr)4] were successfully used as catalysts for the epoxidation-alcoholysis of glycals using hydrogen peroxide [H2O 2]. Reaction substrates included a range of variously protected glycals and different alcohols were used as solvents. Ti(O-i-Pr)4 was only effective in methanol as solvent, but gave methyl glycosides in high yields and high selectivities. The Venturello complex proved to be a very versatile and efficient catalyst. Apart from epoxidation-alcoholysis in alcoholic solvents it also showed activity in biphasic conditions to allow for glycosylation of long-chain alcohols and was very effective in the stereoselective dihydroxylation of benzylated glucal.

C-GLYCOSIDE ANALOGUES OF N-(4-HYDROXYPHENYL)RETINAMIDE-O-GLUCURONIDE

The present invention provides breast cancer chemopreventive arylamide analogues of retinoic acid, more particularly C-glycoside analogues of N-(4-hydroxyphenyl)retinamide-O-glucuronide and N-glycoside analogue of retinoyl beta-glucuronide that resist both beta-glucuronidase mediated enzymatic hydrolysis as well as acid catalyzed hydrolysis. Specifically, the drugs include 4-(retinamido)phenyl-C-glucuronide; 4-(retinamido)phenyl-C-glucoside; 4-(retinamido)benzyl-C-xyloside; 4-(retinamido)benzyl-C-glucoside; 4-(retinamido)benzyl-C-glucuronide; 4-(retinamido)phenyl-C-xyloside, 1-(B-D-lucopyranosyl) retinamide and 1-(D-glucopyranosyluronosly) retinamide. The invention also relates to a method for making such drugs.

PYRIDINDOLOL ANALOGUES. SYHTHESIS OF 3-HYDROXYMETHYL-1-(POLYHYDROXYALKYL)-β-CARBOLINES

Peracetylated (D)-glucose, (D)-galactose, (D)-ribose, (L)-arabinose and (D)-xylose have been subjected to a Pictet-Spengler cyclisation with methyl tryptophanate to give β-carboline derivatives which have been converted to a series of pyridindolol analogues.