5155-43-1

Usage

Uses

Used in Organic Synthesis:
METHYL-6-DEOXY-A-D-GLUCOPYRANOSIDE is used as a key intermediate for the preparation of various glycosides. Its unique structure allows for the formation of diverse glycosidic linkages, which are essential for the synthesis of complex natural products and pharmaceuticals.
Used in Carbohydrate Chemistry Research:
In the field of carbohydrate chemistry, METHYL-6-DEOXY-A-D-GLUCOPYRANOSIDE serves as a valuable compound for studying the properties and reactions of glycosides. Its presence enables researchers to explore the structural and functional aspects of carbohydrates and their interactions with other biomolecules.
Used in Biochemistry Research:
METHYL-6-DEOXY-A-D-GLUCOPYRANOSIDE is utilized as a building block in biochemistry research, particularly for the synthesis of biologically active compounds and the investigation of carbohydrate-mediated biological processes. Its unique structure provides opportunities for the development of novel bioactive molecules and the understanding of carbohydrate-based interactions in biological systems.

Upstream product

• 67-56-1 methanol 
• 73-34-7 6-deoxy-L-galactose 
• 73139-33-0 methyl-2,3-di-O-acetyl-4-O-benzoyl-6-desoxy-α-D-arabino-hex-5-enopyranoside 
• 24332-97-6 Methyl 2,3,4-tri-O-acetyl-6-deoxy-β-L-galactopyranoside 
• 7647-01-0 hydrogenchloride 
• 2438-80-4 L-Fucose 
• 2774-23-4 methyl 2-O-acetyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 6752-75-6 methyl-2,3-di-O-acetyl-4,6-O-benzylidene-α-D-altropyranoside 
• 92418-38-7 (3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate 
• 6340-57-4 methyl 2,3,4-tri-O-acetyl-6-deoxy-β-D-glucopyranoside 
• 122204-71-1 methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-β-D-glucopyranoside 
• 19940-17-1 methyl 2,3,4-tri-O-acetyl-6-deoxy-α-D-glucopyranoside 
• 51236-53-4 methyl 2,3,4-tri-O-benzoyl-6-deoxy-α-D-glucopyranoside 
• 6619-09-6 methyl 6-O-tosyl-α-D-glucopyranoside 

Downstream Products

• 14064-39-2 L-galacto-2,4,5-Trihydroxy-3-methoxy-hexanal 
• 135041-33-7 methyl 3-O-benzyl-β-L-fucopyranoside 
• 14686-83-0 C₂₁H₂₂O₇ 
• 87171-57-1 methyl 2,3,4-tri-O-(p-bromobenzoyl)-β-L-fucopyranoside 
• 170998-60-4 Methyl 2-O-acetyl-4-O-benzoyl-6-deoxy-β-L-galactopyranoside 
• 170998-67-1 Methyl 2-O-acetyl-4-O-benzoyl-6-deoxy-β-L-xylo-hexopyranosid-3-ulose 
• 112047-81-1 O³-methyl-L-lyxo-6-deoxy-[2]hexosulose-bis-phenylhydrazone 
• 14917-71-6 methyl-(O³,O⁴-isopropylidene-O²-methyl-β-L-fucopyranoside) 
• 1379777-16-8 methyl 3-O-phenoxythiocarbonyl-β-L-fucopyranoside 
• 1128-40-1 methyl 6-deoxy-β-L-glucopyranoside 
• 134311-92-5 methyl-2,4-di-O-benzyl-β-D-quinovopyranoside 
• 176380-03-3 methyl 2,3‐di‐O‐benzyl‐6‐deoxy‐β‐D‐glucopyranoside 
• 197657-27-5 methyl-2-O-benzyl-β-D-quinovopyranoside 
• 51288-33-6 C₂₁H₂₂O₇ 

Relevant academic research and scientific papers

Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation

A Cu(II)-catalyzed diastereoselective Michael/aldol cascade approach is used to accomplish concise total syntheses of cardiotonic steroids with varying degrees of oxygenation including cardenolides ouabagenin, sarmentologenin, 19-hydroxysarmentogenin, and 5-epi-panogenin. These syntheses enabled the subsequent structure activity relationship (SAR) studies on 37 synthetic and natural steroids to elucidate the effect of oxygenation, stereochemistry, C3-glycosylation, and C17-heterocyclic ring. Based on this parallel evaluation of synthetic and natural steroids and their derivatives, glycosylated steroids cannogenol-l-α-rhamnoside (79a), strophanthidol-l-α-rhamnoside (92), and digitoxigenin-l-α-rhamnoside (97) were identified as the most potent steroids demonstrating broad anticancer activity at 10-100 nM concentrations and selectivity (nontoxic at 3 μM against NIH-3T3, MEF, and developing fish embryos). Further analyses indicate that these molecules show a general mode of anticancer activity involving DNA-damage upregulation that subsequently induces apoptosis.

Calcium hypophosphite mediated deiodination in water: Mechanistic insights and applications in large scale syntheses of d-quinovose and d-rhamnose

The inorganic calcium hypophosphite was found to be a cheap, non-toxic, water-soluble and environmentally friendly reducing reagent for radical deiodination in water. Thorough mechanism studies revealed that calcium hypophosphite was oxidized to water insoluble calcium phosphite which was the major co-product of the deiodination reaction. Based on this observation, a practical synthesis of rare d-quinovose and d-rhamnose from cheap and commercially available materials on a hundred-mmol scale was reported.

Synthesis of Deoxyglycosides by Desulfurization under UV Light

This study was performed to develop a highly efficient method whereby desulfurization could be completed in 0.5 h under ultraviolet light, at room temperature, and in the presence of trialkylphosphine. Using this method, deoxyglycosides could be produced from sulfur-containing glycosides in almost quantitative yields. The much higher reactivity of desulfurization with triethylphosphine versus that with triethylphosphite is also discussed.

Synthesis of MeON-neoglycosides of digoxigenin with 6-deoxy- and 2,6-dideoxy-D-glucose derivatives and their anticancer activity

Cardiac glycosides show anticancer activities and their deoxy-sugar chains are vital for their anticancer effects. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and get more potent anticancer agents, a series of MeON-neoglycosides of digoxigenin was synthesized and evaluated. First, ten 6-deoxy- and 2,6-dideoxy-D-glucopyranosyl donors were synthesized starting from methyl α-D-glucopyranoside and 2-deoxy-D-glucose. Meanwhile, the digoxigenin was obtained by acidic hydrolysis of commercially available digoxin as glycosyl acceptor. Then, a 22-member MeON-neoglycoside library of digoxigenin was successfully synthesized by neoglycosylation method. Finally, the induction of Nur77 expression and its translocation from the nucleus to cytoplasm together with cytotoxicity of these MeON-neoglycosides were evaluated. The SAR analysis revealed that C3 glycosylation is required for their induction of Nur77 expression. Moreover, some MeON-neoglycosides (2b and 8b) could significant induce the expression of Nur77 and its translocation from the nucleus to cytoplasm. However, these compounds showed no inhibitory effects on the proliferation of cancer cells, suggesting that they may not induce apoptosis of NIH-H460 cancer cells and their underlying potential and application toward cancer cells deserves future study.

Synthesis of β-(1→2)-Linked 6-Deoxy- l -altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor

The β-(1→2)-linked 6-deoxy-l-altropyranose di- to pentasaccharides 2-5, relevant to the O-antigen of the infectious Yersinia enterocolitica O:3, were synthesized for the first time. The challenging 1,2-cis-altropyranosyl linkage was assembled effectively via glycosylation with 2-O-benzyl-3,4-di-O-benzoyl-6-deoxy-l-altropyranosyl ortho-hexynylbenzoate (7) under the catalysis of PPh3AuNTf2. NMR and molecular modeling studies showed that the pentasaccharide (5) adopted a left-handed helical conformation.

Direct glycosylation of unprotected and unactivated sugars using bismuth nitrate pentahydrate

Bi(NO3)3, a low-cost, mild, and environmentally green catalyst, has been successfully utilized for Fischer glycosylation for the synthesis of alkyl/aryl glycopyranosides by reacting unprotected sugars, namely, D-glucose, L-rhamnose, D-galactose, D-arabinose, and N-acetyl-D-glucosamine with various alcohols in good to excellent yields. The glycosides were formed with high α-selectivity. Further, an expedient separation of α- and β-glycosides using silver nitrate-impregnated silica gel flash liquid chromatography has been developed.

Catalytic and regioselective oxidation of carbohydrates to synthesize keto-sugars under mild conditions

A new catalytic and regioselective approach for the synthesis of keto-sugars is described. An organotin catalyst, Oc2SnCl2, in the presence of trimethylphenylammonium tribromide ([TMPhA]+Br3-) accelerates the regioselective oxidation at the axial -OH group of 1,2-diol moieties in galactopyranosides. The reaction conditions can also be used for the regioselective oxidation of various carbohydrates.

NaBH3CN and other systems as substitutes of tin and silicon hydrides in the light or heat-initiated reduction of halosugars: A tunable access to either 2-deoxy sugars or 1,5-anhydro-itols

UV light-promoted reduction of acetobromoglucose by NaBH3CN in t-BuOH afforded 1,3,4,6-tetra-O-acetyl-2-deoxy-α-d-arabino-hexopyranose in high yield and purity, via a Surzur-Tanner rearrangement, while, with 10 mol % thiophenol added, acetylated 1,5-anhydro-d-glucitol was cleanly obtained. Such tin-free and mild reductions, presumed to proceed via radical pathways, were more efficient with NaBH3CN compared to NaBH4 or NaBD 4, and do not occur with acetochloroglucose. Similar reductions to 1,3,4,6-tetra-O-acetyl-2-deoxy-α-d-arabino-hexopyranose were achieved upon heating to 80 C t-BuOH or CH3CN solutions of NaBH3CN and AIBN, but with a lower selectivity due to competing ionic reactions. With other pyranosyl bromides, reductions by NaBH3CN could be tuned similarly (d-galacto), but some (d-manno, 5-thio-d-xylo) gave mainly or exclusively 1,5-anhydro-itols. Other conditions, or reagents promoting SET process, afforded also reduced products, but with lower rates or selectivities. Primary iodides were reduced readily with NaBH3CN under UV light.

Characterization of ulvan extracts to assess the effect of different steps in the extraction procedure

An effective application development of the polysaccharide ulvan requires a comprehensive knowledge about the influence of the extraction process on composition of the extracts and in ulvan itself. In this context, the two main objectives of the present work are (1) the establishment of an efficient extraction process for ulvan and (2) development of an accurate characterization methodology to evaluate the extract composition and ulvan content. Three ulvan-rich extracts obtained by different schemes of extraction were studied. The methodology for the analysis was improved and a detailed analysis of extracted ulvan was provided. The polysaccharide is rich in ulvanobiuronic acid 3-sulfate type A [→4)-β-d-GlcAp-(1 → 4)-α-l-Rhap 3S-(1→], with minor amounts of ulvanobiuronic acid 3-sulfate type B [→4)-α-l-IdoAp-(1 → 4)-α-l-Rhap 3S-(1→]. The extract with the higher degree of purification is a high molecular weight polysaccharide (790 kDa) composed of rhamnose (22.4%), glucuronic acid (22.5%), xylose (3.7%), iduronic acid (3.1%) and glucose (1.0%). It is highly sulfated (32.2%) and contains 1.3% of proteins and 10.3% of inorganic material. Applying simple extraction scheme it was possible to obtain an extract from green algae with high content of ulvan without affecting the overall chemical structure of the polysaccharide.

Organotin-catalyzed highly regioselective thiocarbonylation of nonprotected carbohydrates and synthesis of deoxy carbohydrates in a minimum number of steps

Nonprotected carbohydrates: The catalytic regioselective thiocarbonylation of carbohydrates by using organotin dichloride under mild conditions was demonstrated. The reaction afforded various deoxy saccharides in high yields and excellent regioselectivity in a minimum number of steps. The regioselectivity of the thiocarbonylation is attributed to the intrinsic character of the carbohydrates based on the stereorelationship of their hydroxy groups (see scheme). Copyright