22277-65-2

Upstream product

• 67-56-1 methanol 
• 530-26-7 D-Mannose 
• 124-41-4 sodium methylate 
• 7732-18-5 water 
• 2460-41-5 methyl β-D-arabino-hexopyranosid-2-ulose 
• 64-17-5 ethanol 
• 7647-01-0 hydrogenchloride 
• 3458-28-4 D-Mannose 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 709-50-2 methyl beta-D-glucopyranoside 
• 18276-53-4 1-(trimethylsilyl)-1H-pyrrole 
• 110744-71-3 acanthacerebroside A 
• 7404-42-4 D-Mannose-dibenzyldithioacetal 
• 131488-68-1 (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triol 

Downstream Products

• 64952-14-3 (R)-3-hydroxy-2-((R)-1-methoxy-2-oxo-ethoxy)-propionaldehyde 
• 4148-71-4 methyl exo-2,3:4,6-di-O-benzylidene-β-D-mannopyranoside 
• 4148-71-4 methyl endo-2,3:4,6-di-O-benzylidene-β-D-mannopyranoside 
• 4148-71-4 methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 71526-33-5 methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 131283-82-4 methyl 6-O-tert-butyldiphenylsilyl-β-D-mannopyranoside 
• 64-18-6 formic acid 
• 51224-38-5 methyl β-D-altropyranoside 
• 709-50-2 methyl beta-D-glucopyranoside 
• 3162-96-7 Methyl-4,6-O-(phenylmethylene)-β-D-mannopyranoside 
• 686299-10-5 methyl L-glycero-α-D-manno-heptopyranoside 
• 86342-19-0 methyl 2,4-di-O-benzyl-β-D-mannopyranoside 
• 57783-73-0 methyl 3,4-di-O-benzyl-β-D-mannopyranoside 

Relevant academic research and scientific papers

Carbon glycoside glycosylated tetravalent platinum compound as well as synthesis method and application thereof

The invention provides a carbon glycoside glycosylated tetravalent platinum compound, a synthesis method and application thereof. R1 and R2 are independently C1-C4 lower alkanes, R3 is glucose, galactose, mannose and ribose, different sugars are used as raw materials, and a series of carbon glycoside glycosylated tetravalent platinum compounds are synthesized through protection and deprotection reaction and metallization reaction of the sugars. The synthesis method is simple, the used raw materials are cheap and easy to obtain, the glycosylated tetravalent platinum compound has the capacity of targeting glucose transporter protein and has potential application value in the field of cancer treatment, introduction of a C-glucosidic bond enables the series of compounds to have the capacity of resisting hydrolysis of beta-glucosidase, and the compound is expected to be applied to the field of oral antitumor drugs.

Calixanthomycin A: Asymmetric Total Synthesis and Structural Determination

We report the first asymmetric total synthesis and structural determination of calixanthomycin A. Taking advantage of a modular strategy, a concise approach was developed to assemble the hexacyclic skeleton with both enantiomers of the lactone A ring. Stereoselective glycosylation coupled the angular hexacyclic framework with a monosaccharide fragment to produce calixanthomycin A and its stereoisomers. This enable us to determine and assign the absolute configuration of C-25 (25S) and monosaccharide (derivative of l-glucose).

Chemical constituents of the aerial parts of Algerian Galium brunneum: Isolation of new hydroperoxy sterol glucosyl derivatives

The liposoluble extract of Galium brunneum aerial parts from North-eastern Algeria was chemically investigated. The EtOAc soluble portion contained a series of glycosyl cucurbitacins and sterols including three new glucosyl hydroperoxy sterols 1–3 among other phenolic components whereas the BuOH soluble fraction was dominated by glycosyl derivatives of flavonoids, iridoids and lignans, according to the chemistry reported in the literature for the genus Galium. The structure of new oxidized sterols 1–3 was determined by spectroscopic methods as well as by comparison with related known metabolites. Selected main compounds from both extracts, which revealed moderate antibacterial activities, were tested for their growth inhibitory properties against Gram-positive and Gram-negative bacteria. This is the first report of cucurbitacins in plants of genus Galium.

Structure of the unusual Sinorhizobium fredii HH103 lipopolysaccharide and its role in symbiosis

Rhizobia are soil bacteria that form important symbiotic associations with legumes, and rhizobial surface polysaccharides, such as K-antigen polysaccharide (KPS) and lipopolysaccharide (LPS), might be important for symbiosis. Previously, we obtained a mutant of Sinorhizobium fredii HH103, rkpA, that does not produce KPS, a homopolysaccharide of a pseudaminic acid derivative, but whose LPS electrophoretic profile was indistinguishable from that of the WT strain. We also previously demonstrated that the HH103 rkpLMNOPQ operon is responsible for 5-acetamido-3,5,7,9-tetradeoxy-7-(3-hydroxybutyramido)-L-glyc-ero-L-manno-nonulosonic acid [Pse5NAc7(3OHBu)] production and is involved in HH103 KPS and LPS biosynthesis and that an HH103 rkpM mutant cannot produce KPS and displays an altered LPS structure. Here, we analyzed the LPS structure of HH103 rkpA, focusing on the carbohydrate portion, and found that it contains a highly heterogeneous lipid A and a peculiar core oligosaccharide composed of an unusually high number of hexuronic acids containing b-configured Pse5NAc7(3OHBu). This pseudaminic acid derivative, in its a-configuration, was the only structural component of the S. fredii HH103 KPS and, to the best of our knowledge, has never been reported from any other rhizobial LPS. We also show that Pse5NAc7(3OHBu) is the complete or partial epitope for a mAb, NB6-228.22, that can recognize the HH103 LPS, but not those of most of the S. fredii strains tested here. We also show that the LPS from HH103 rkpM is identical to that of HH103 rkpA but devoid of any Pse5NAc7(3OHBu) residues. Notably, this rkpM mutant was severely impaired in symbiosis with its host, Macroptilium atropurpureum.

From d-to l-Monosaccharide Derivatives via Photodecarboxylation-Alkylation

Photodecarboxylation-alkylation of conformationally locked monosaccharides leads to inversion of stereochemistry at C5. This allows the synthesis of l-sugars from their readily available d-counterparts. Via this strategy, methyl l-guloside was synthesized from methyl d-mannoside in 21% yield over six steps.

Methyl glycosides via Fischer glycosylation: translation from batch microwave to continuous flow processing

Abstract: A continuous flow procedure for the synthesis of methyl glycosides (Fischer glycosylation) of various monosaccharides using a heterogenous catalyst has been developed. In-depth analysis of the isomeric composition was undertaken and high consistency with corresponding results observed under microwave heating was obtained. Even in cases where addition of water was needed to achieve homogeneity—a prerequisite for the flow experiments—no detrimental effect on the conversion was found. The scalability was demonstrated on a model case (mannose) and as part of the target-oriented synthesis of d-glycero-d-manno heptose, both performed on multigram scale.

Production of lactic acid derivatives from sugars over post-synthesized Sn-Beta zeolite promoted by WO3

Various metal oxides were used as co-catalysts to improve the production of alkyl lactate over Sn-Beta-P. WO3 exhibited the best promotion effect. The yield of MLA increased from 25% (6.5 g L?1) over Sn-Beta-P (0.2 g) to 52% (13.4 g L?1) over WO3 (0.1 g) and Sn-Beta-P (0.1 g) at 160 °C for 5 h and 3.1 wt% of glucose concentration. MLA yield of 38% was attained even at glucose concentration of 10 wt% and the space-time yield reached 7.1 g L?1 h?1. The action mechanism of WO3 was investigated. Fine WO3 particles adsorbed on surface of Sn-Beta-P in reaction media and decreased the silanol defects of Sn-Beta-P. This promotes retro-aldol of fructose, the rate-determining step of whole reaction, thus facilitated the formation of MLA. Kinetic studies indicate that the presence of WO3 decreased the activation energy of the retro-aldol of fructose. The binary solid WO3 and Sn-Beta-P is recyclable.

Catalytic glycosylation of glucose with alkyl alcohols over sulfonated mesoporous carbons

Herein we investigated the catalytic performances of sulfonated mesoporous carbons in the glycosylation of carbohydrates with alkyl alcohols. Catalytic performances were compared to common solid acid catalysts previously reported for this reaction. Under optimized conditions, the targeted alkyl glycosides were obtained in 85% yield, together with a turn over frequency and a space time yield higher than those of the best heterogeneous catalysts reported so far in such reaction. Furthermore, the presence of mesoporous channels significantly lowered the deactivation rate of the catalyst in comparison to a non-porous sulfonated carbon.

Kinetically Controlled Fischer Glycosidation under Flow Conditions: A New Method for Preparing Furanosides

Kinetically controlled Fischer glycosidation was achieved under flow conditions. β-Hydroxy-substituted sulfonic acid functionalized silica (HO-SAS) was used as an acid catalyst. This reaction directly converted aldohexoses into kinetically favored furanosides to enable the practical synthesis of furanosides. After optimization of the reaction temperature and residence time, glucofuranosides, galactofuranosides, and mannofuranosides were synthesized in good yields.

Synthesis of Rare Deoxy Amino Sugar Building Blocks Enabled the Total Synthesis of a Polysaccharide Repeating Unit Analogue from the LPS of Psychrobacter cryohalolentis K5T

Lipopolysaccharides (LPSs) play key roles in humoral immunity. Recently, the LPS structure of the Psychrobacter cryohalolentis K5T strain was reported. Due to the presence of unnatural amino sugars and branched linkages, its structure is unique. Herein we report the total synthesis of an LPS analogue of P. cryohalolentis K5T. After overcoming the issues like ring conformation changes and elimination of triflate, we were able to develop a strategy for the synthesis of the newly reported 2,3,4-triacetamido-2,3,4-trideoxy-l-arabinose derivative. Coupling of different donors with suitable acceptors from the nonreducing end to the reducing end and further functional group modifications delivered the protected LPS hexasaccharide repeating unit. After functional group modifications, we were unable to oxidize the hindered primary hydroxyl group to synthesize the target molecule. Alternatively, removal of the permanent protecting groups afforded the LPS hexasaccharide repeating unit analogue of Psychrobacter cryohalolentis K5T.