86334-50-1

Upstream product

• 3615-37-0 D-Fucose 
• 67-56-1 methanol 
• 7208-41-5 penta-O-acetyl-6-deoxy-L-glucitol 
• 2914-23-0 barium methoxide 
• 35867-45-9 6-deoxy-L-glucose 
• 32469-26-4 (3R,4R,5S)-5-((R)-1,2-Bis-trimethylsilanyloxy-ethyl)-3,4-bis-trimethylsilanyloxy-dihydro-furan-2-one 
• 6322-07-2 D-gulono-1,4-lactone 
• 3891-58-5 tetra-O-acetyl-D-xylose 
• 6014-42-2 L-rhamnose 
• 488-28-8 hexane-1,2,3,4,5-pentaol 
• 13074-06-1 L-fucitol 
• 2438-80-4 L-Fucose 
• 116180-60-0 ((4R,5S)-2,2-dimethyl-5-((4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)-1,3-dioxolan-4-yl)methanol 
• 86334-49-8 (2R,3S,4R,5R)-6,6-Bis-ethylsulfanyl-hexane-1,2,3,4,5-pentaol 

Downstream Products

• 488-28-8 racemic rhodeitol 
• 86296-06-2 1-O-trityl-L-epirhamnitol 
• 123594-91-2 Anthracene-9-carboxylic acid (2R,3S,4S,5S)-2,3,4,5-tetrakis-[(E)-3-(4-methoxy-phenyl)-acryloyloxy]-hexyl ester 
• 86296-07-3 Acetic acid (1R,2S,3S,4S)-2,3,4-triacetoxy-1-trityloxymethyl-pentyl ester 

Relevant academic research and scientific papers

Effect of carbon chain length on catalytic C–O bond cleavage of polyols over Rh-ReOx/ZrO2 in aqueous phase

Production of linear deoxygenated C4 (butanetriols, -diols, and butanols), C5 (pentanetetraols, -triols, -diols, and pentanols), and C6 products (hexanepentaols, -tetraols, -triols, -diols, and hexanols) is achievable by hydrogenolysis of erythritol, xylitol, and sorbitol over supported-bimetallic Rh-ReOx (Re/Rh molar ratio 0.5) catalyst, respectively. After validation of the analytical methodology, the effect of some reaction parameters was studied. In addition to C–O bond cleavage by hydrogenolysis, these polyols can undergo parallel reactions such as epimerization, cyclic dehydration, and C–C bond cleavage. The time courses of each family of linear deoxygenated C4, C5, and C6 products confirmed that the sequence of appearance of the different categories of deoxygenated products followed a multiple sequential deoxygenation pathway. The highest selectivity to a mixture of linear deoxygenated C4, C5, and C6 products at 80percent conversion was favoured under high pressure in the presence of 3.7wt.percentRh-3.5wt.percentReOx/ZrO2 catalysts (54–71percent under 80 bar) at 200 °C.

Triacetonide of Glucoheptonic Acid in the Scalable Syntheses of d -Gulose, 6-Deoxy- d -gulose, l -Glucose, 6-Deoxy- l -glucose, and Related Sugars

Ease of separation of petrol-soluble acetonides derived from the triacetonide of methyl glucoheptonate allows scalable syntheses of rare sugars containing the l-gluco or d-gulo structural motif with any oxidation level at the C6 or C1 position of the hexose, usually without chromatography: meso-d-glycero-d-guloheptitol available in two steps is an ideal entry point for the study of the biotechnological production of heptoses.

Synthesis of novel l-rhamnose derived acyclic C-nucleosides with substituted 1,2,3-triazole core as potent sodium-glucose co-transporter (SGLT) inhibitors

Sodium-glucose co-transporter (SGLT) inhibitors are a novel class of therapeutic agents for the treatment of type 2 diabetes by preventing renal glucose reabsorption. In our efforts to identify novel inhibitors of SGLT, we synthesized a series of l-rhamnose derived acyclic C-nucleosides with 1,2,3-triazole core. The key β-ketoester building block 4 prepared from l-rhamnose in five steps, was reacted with various aryl azides to produce the respective 1,2,3-triazole derivatives in excellent yields. Deprotection of acetonide group gave the desired acyclic C-nucleosides 7a-o. All the new compounds were screened for their sodium-glucose co-transporters (SGLT1 and SGLT2) inhibition activity using recently developed cell-based nonradioactive fluorescence glucose uptake assay. Among them, 7m with IC50: 125.9 nM emerged as the most potent SGLT2 inhibitor. On the other hand compound 7d exhibited best selectivity for inhibition of SGLT2 (IC50: 149.1 nM) over SGLT1 (IC50: 693.2 nM). The results presented here demonstrated the utility of acyclic C-nucleosides as novel SGLT inhibitors for future investigations.