34819-86-8

Usage

InChI:InChI=1/C10H14O5/c1-6-10(15-8(3)12)9(4-5-13-6)14-7(2)11/h4-6,9-10H,1-3H3/t6-,9-,10-/m0/s1

Upstream product

• 39524-38-4 2,3,4-tri-O-acetyl-6-deoxy-beta-L-mannopyranosyl bromide 
• 116050-47-6 Acetic acid (2S,3S,4S)-3-acetoxy-2-methyl-6-(pyridin-2-ylsulfanyl)-tetrahydro-pyran-4-yl ester 
• 14133-63-2 methyl 2,3-O-isopropylidene-α-L-rhamnoside 
• 5158-64-5 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide 
• 5160-09-8 2,3,4‐tri‐O‐acetyl-α-L‐rhamnopyranosyl chloride 
• 64-19-7 acetic acid 
• 127-09-3 sodium acetate 
• 73-34-7 L-rhamnose 
• 108-24-7 acetic anhydride 
• 30021-94-4 1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 
• 73-34-7 6-deoxy-L-glucose 
• 883884-80-8 1,2,3,4-tetra-O-acetyl-L-rhamnose 
• 75-36-5 acetyl chloride 
• 53657-42-4 L-rhamnal 

Downstream Products

• 53657-42-4 L-rhamnal 
• 239806-31-6 4'-(5-O-acetyl-2,6-anhydro-1,3,4,7-tetradeoxy-α-L-erythro-hept-3-enitol-1-yl)iodobenzene 

Relevant academic research and scientific papers

Synthetic routes toward pentasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O181

An efficient synthetic strategy has been developed for the synthesis of the pentasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O181. A one-pot, two step iterative glycosylation and [2 + 3] block glycosylation strategy have been adopted for the construction of the pentasaccharide derivative 2, which was then transformed into target compound 1 after a series of functional group transformations. Here H2SO4-silica has been used successfully as a promoter for all glycosylation reaction. The stereoselective outcomes of all glycosylation reactions were very good. The 2-acetamido-2,6-dideoxy-L-glucose (L-QuipNAc) building block was obtained from known carbohydrate L-rhamnose precursors.

An expeditious stereoselective synthesis of natural (-)-Cassine via cascade HWE [3 + 2]-cycloaddition process

l-Rhamnose is transformed to (-)-Cassine via a remarkable four step one pot reaction. The Horner-Wadsworth-Emmons [3 + 2]-1,3-dipolar cycloaddition reaction cascade is the pivotal step in this reaction sequence and makes the synthesis highly efficient. The Royal Society of Chemistry 2006.

Expeditious Synthesis of a Tetrasaccharide Repeating Unit of the O-Antigen of Escherichia coli O163

The synthesis of the tetrasaccharide repeating unit of the O-antigen of Escherichia coli O163 as its p-methoxyphenyl (PMP) glycoside was achieved followed by sequential glycosylation strategy through thioglycoside activation using sulfuric acid immobilized on silica (H2SO4-silica) in conjunction with N-iodosuccinimide as a Bronsted acid catalyst. The application of one-pot reaction conditions for two glycosylations and in situ PMB-group removal reduced the number of reaction steps significantly. The l-QuipNAc building block was obtained from known carbohydrate l-rhamnose precursors. The stereoselective outcomes of all glycosylation reactions were found to be very good. A late-stage TEMPO-mediated oxidation was performed for the formation of required uronic acid moiety. An analogue of the target tetrasaccharide was also prepared by using one-pot glycosylation approach. Such synthetic oligosaccharides could later be effectively conjugated with an appropriate protein to furnish glycoconjugate derivatives for their use in immunochemical studies.

Chaunopyran A: Co-Cultivation of Marine Mollusk-Derived Fungi Activates a Rare Class of 2-Alkenyl-Tetrahydropyran

Co-cultivation of Chaunopycnis sp. (CMB-MF028) and Trichoderma hamatum (CMB-MF030), fungal strains co-isolated from the inner tissue of an intertidal rock platform mollusc (Siphonaria sp), resulted in transcriptional activation of a rare class of 2-alkenyl-tetrahydropyran, chaunopyran A (7), and biotransformation and deactivation of the antifungal pyridoxatin (1), to methyl-pyridoxatin (8). This study illustrates the complexity of offensive and counter-offensive molecular defenses encountered during fungal co-cultivation, and the opportunities for activating new, otherwise transcriptionally silent secondary metabolites.

Automated, Multistep Continuous-Flow Synthesis of 2,6-Dideoxy and 3-Amino-2,3,6-trideoxy Monosaccharide Building Blocks

An automated continuous flow system capable of producing protected deoxy-sugar donors from commercial material is described. Four 2,6-dideoxy and two 3-amino-2,3,6-trideoxy sugars with orthogonal protecting groups were synthesized in 11–32 % overall yields in 74–131.5 minutes of total reaction time. Several of the reactions were able to be concatenated into a continuous process, avoiding the need for chromatographic purification of intermediates. The modular nature of the experimental setup allowed for reaction streams to be split into different lines for the parallel synthesis of multiple donors. Further, the continuous flow processes were fully automated and described through the design of an open-source Python-controlled automation platform.

Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement

Stereoselective glycosylation is challenging in carbohydrate chemistry. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside and α-sulfoxide-glucoside, respectively.

Preparation method and application of first-class rhamnose C-glycoside

The invention provides a rhamnose C-glycoside drug. The structural formula is shown as below, wherein R1 comprises a phenyl group, a substituted phenyl group, and various alkyl groups of C1 to C10, R2comprises a phenyl group and a substituted phenyl group, and the substituted phenyl groups of the R1 and the R2 comprise alkyl groups, halogen atoms, alkoxy groups and alkylthio-substituted phenyl groups. A preparation method of the rhamnose C-glycoside drug includes acetylating and brominating rhamnose in sequence to obtain the rhamnose C-glycoside drug. The prepared product is applied to preparation of drugs resistant to gastric cancer, breast cancer and liver cancer.

Tuning the Chemoselectivity of Silyl Protected Rhamnals by Temperature and Br?nsted Acidity: Kinetically Controlled 1,2-Addition vs Thermodynamically Controlled Ferrier Rearrangement

An acidity- and temperature-dependent chemoselective glycosylation of silyl-protected rhamnals with alcohols has been revealed. The reaction undergoes a 1,2-addition pathway with (±)-CSA as the catalyst at rt, affording kinetically controlled 2-deoxyl rhamnosides. In contrast, only thermodynamically controlled 2,3-unsaturated rhamnosides are formed via Ferrier rearrangement when elevating reaction temperature to 85 °C or using CF3SO3H instead. This tunable glycosylation allows facile and practical access to both 2-deoxyl and 2,3-unsaturated rhamnosides with excellent yields and high α-stereoselectivity.

Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals

A novel synthetic route for highly substituted conjugated ketones has been developed utilizing glycals as starting materials. The two-step process combined the Heck reaction/Lewis acid promoted ring opening to afford the products in 33–80 % overall yields and with a high level of trans stereoselectivity. Since the products are essentially the aldols, this methodology may be employed in some cases as an alternative synthetic route to the typical aldol condensation. Densely substituted, selectively protected conjugated ketones are synthetically attractive structures which, in our case, proved to be biologically equally appealing. Namely, they showed activity against several cancer cell lines, such as HeLa, K562, MDA-MB-453, in some instances overperforming cisplatin used as a standard.

Palladium catalyzed stereocontrolled synthesis of C-aryl glycosides using glycals and arenediazonium salts at room temperature

A stereocontrolled synthesis of aryl-C-glycosides was achieved using glycals and aryldiazonium salts in the presence of palladium acetate. A wide range of glycals including d-glucal, d-galactal, l-rhamnal, d-xylal and d-ribal underwent C-arylation at the anomeric carbon in the presence of different aryldiazonium tetrafluoroborates and gave synthetically useful 2,3-deoxy-3-keto-α-aryl-C-glycosides in good to excellent yields. Broad substrate scope, simple operation and room temperature reactions make this protocol very attractive in organic synthesis.