102517-74-8

Basic information

• Product Name: methyl 6-deoxy-β-L-altropyranoside
• CAS NO: 102517-74-8
• Molecular Weight: 178.185
• Mol File: 102517-74-8.mol

Chemical Properties

• CAS DataBase Reference: methyl 6-deoxy-β-L-altropyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 6-deoxy-β-L-altropyranoside(102517-74-8)
• EPA Substance Registry System: methyl 6-deoxy-β-L-altropyranoside(102517-74-8)

Safety Data

• Hazardous Substances Data: 102517-74-8(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 2438-80-4 L-Fucose 
• 73139-33-0 methyl-2,3-di-O-acetyl-4-O-benzoyl-6-desoxy-α-D-arabino-hex-5-enopyranoside 
• 6340-57-4 methyl 2,3,4-tri-O-acetyl-6-deoxy-β-D-glucopyranoside 
• 7404-26-4 methyl 6-bromo-6-deoxy-β-D-glucopyranoside 
• 53942-13-5 Methyl 2,3,4-Tri-O-acetyl-6-deoxy-β-D-galactopyranoside 
• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 
• 15814-59-2 (2S,3S,4S,5S,6R)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 1374788-87-0 3-O-{[α-L-rhamnopyranosyl(1->4)][β-D-glucopyranosyl(1->6)]-β-D-glucopyranosyl}-26-O-β-D-glucopyranosyl-(25S)-5β-furostane-3β,22,26-triol 
• 24333-07-1 sarsaparilloside 
• 24332-93-2 Δ(20(22))-sarsaparilloside 
• 19057-61-5 parillin 
• 100201-60-3 sophoraflavoside I 
• 73-34-7 D-Fucose 

Downstream Products

• 14064-39-2 L-galacto-2,4,5-Trihydroxy-3-methoxy-hexanal 
• 171228-79-8 Methyl 3,4-O-(R)-benzylidene-6-deoxy-β-L-galactopyranoside 
• 171228-78-7 Methyl 3,4-O-(S)-benzylidene-6-deoxy-β-L-galactopyranoside 
• 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 
• 51236-57-8 C₂₁H₂₂O₇ 
• 197657-35-5 methyl 2-O-benzyl-3-O-(β-D-fucopyranosyl)-β-D-quinovopyranoside 
• 197657-36-6 methyl 2-O-benzyl-3-O-(β-D-fucopyranosyl)-β-D-quinovopyranoside 
• 197657-39-9 methyl 4-O-benzoyl-3-O-(2,4-di-O-benzoyl-3-O-methyl-β-D-fucopyranosyl)-β-D-quinovopyranoside 
• 197657-37-7 methyl 2-O-benzyl-4-O-benzoyl-3-O-(2,4-di-O-benzoyl-β-D-fucopyranosyl)-β-D-quinovopyranoside 

Relevant articles and documents

Caminoside A, an antimicrobial glycolipid isolated from the marine sponge Caminus sphaeroconia.

Extracts of the marine sponge Caminus sphaeroconia showed potent activity in a screen for bacterial type III secretion inhibitors. Bioassay guided fractionation of the extract led to the isolation of the novel antimicrobial glycolipid caminoside A (1). The structure of caminoside A was elucidated by analysis of spectroscopic data and chemical degradation.[structure: see text]

Medicinal foodstuffs. XIII.1 saponin constituents with adjuvant activity from hyacinth bean, the seeds of Dolichos lablab L. (2) : Structures of lablabosides D, E, and F

Following the characterization of lablabosides A, B, and C, new oleanane-type triterpene bisdesmosides, lablabosides D, E, and F, were isolated from the glycosidic fraction with adjuvant activity obtained from the seeds of Dolichos lablab L. (Leguminosae). Their chemical structures were elucidated on the basis of chemical and physicochemical evidence as follows : 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-galactopyranosyl (1→2)-β-D-glucopyranosiduronic acid]-28-O-[6-O-(3-hydroxy-3-methylglutaroyl)-β-D-glucopyranosyl] 24-epi-hederagenin (lablaboside D), 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-galactopyranosyl (1→2)-β-D-glucopyranosiduronic acid]-28-O-[α-L-rhamnopyranosyl (1→4)-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl] 24-epi-hederagenin (lablaboside E), 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-galactopyranosyl (1→2)-β-D-glucopyranosiduronic acid]-28-O-[α-L-rhamnopyranosyl (1→4)-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl] oleanolic acid (lablaboside F).

Phorbasides A-E, cytotoxic chlorocyclopropane macrolide glycosides from the marine sponge Phorbas sp. CD determination of C-methyl sugar configurations

(Chemical Equation Presented) Five new cytotoxic macrolide glycosides phorbasides A-E (3-7), each possessing a macrolide ring appended to a rare ene-yne-trans-2-chlorocyclopropane, were isolated from the same Western Australian sponge (Phorbas sp.) that provided phorboxazoles A and B. The structures of 3-7 were solved by analysis of spectroscopic data including NMR, MS, and CD. A synthesis of methyl 2-O-methyl-α-L-evalose from L-rhamnose was completed and used for configurational assignment of the sugar residue in 3. Acid-catalyzed methanolysis of 3 followed by two-step derivatization of the liberated O-methyl glycoside gave a vicinal 4-O-naphthoyl/tertiary 3-N-(2-aminonaphthyl)carbamate derivative that exhibited exciton coupled CD identical with that of the derivative prepared from synthetic 1,2-O-dimethyl-α-L-evalose.

Carbohydrate molecular recognition: A spectroscopic investigation of carbohydrate-aromatic interactions

The physical basis of carbohydrate molecular recognition at aromatic protein binding sites is explored by creating molecular complexes between a series of selected monosaccharides and toluene (as a truncated model for phenylalanine). They are formed at low temperatures under molecular beam conditions, and detected and characterized through mass-selected, infrared ion depletion spectroscopy - a strategy which exploits the extraordinary sensitivity of their vibrational signatures to the local hydrogen-bonded environment of their OH groups. The trial set of carbohydrates, α- and β-anomers of glucose, galactose and fucose, reflects ligand fragments in naturally occurring protein-carbohydrate complexes and also allows an investigation of the effect of systematic structural changes, including the shape and extent of 'apolar' patches on the pyranose ring, removal of the OH on the exocyclic hydroxymethyl group, and removal of the aglycon. Bound complexes invariably form, establishing the general existence of intrinsic intermolecular potential minima. In most of the cases explored, comparison between recorded and computed vibrational spectra of the bound and free carbohydrates in the absence of solvent water molecules reveal that dispersion forces involving CH-π interactions, which promote little if any distortion of the bound carbohydrate, predominate although complexes bound through specific OH-π hydrogen-bonded interactions have also been identified. Since the complexes form at low temperatures in the absence of water, entropic contributions associated with the reorganization of surrounding water molecules, the essence of the proposed 'hydrophobic interaction', cannot contribute and other modes of binding drive the recognition of sugars by aromatic residues. Excitingly, some of the proposed structures mirror those found in naturally occurring protein-carbohydrate binding sites. the Owner Societies.

STEROIDS OF THE SPIROSTAN AND FUROSTAN SERIES FROM PLANTS OF THE GENUS Allium. II. THE STRUCTURE OF ALLIOSPIROSIDE B FROM Allium cepa

A new steroid glycoside - alliospiroside B (I) - has been isolated from the collective fruit of Allium cepa L.On the basis of chemical transformations and with the aid of physicochemical measurements it has been established that compound (I) has the structure of (25S)spirost-5-ene-1β,3β-diol 1-O- 2)-β-D-galactopyranoside.Compound (I) C39H62O3, mp 200-202 deg C (from ethanol), D20 -110.9 +/- 2 deg (c 1.01; pyridine) was obtained by extracting the collective fruit of A. cepa with ethanol followed by the column chromatographic separation of the combined glycosides on silica gel.The acid hydrolysis of (I) gave (25S)-ruscogenin (II), C27H42O4, mp 189-191 deg C, D23 -104.1 +/- 2 deg (c 0.98; pyridine).The 1H and 13C NMR spectra are given for both compounds and the IR spectrum for compound (I).

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.

Two new antifungal saponins from the Tibetan herbal medicine Clematis tangutica

Bioassay-guided fractionation of the ethanol extract of the aerial parts of Clematis tangutica led to the isolation of two new antifungal triterpene saponins. Their structures were determined to be 3-O-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl ester (1) and 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl ester (2) on the basis of spectral data and chemical evidence. Inhibitory activities of the two saponins against seven fungal strains were evaluated. Compounds 1 and 2 showed evident antifungal activity (MIA ≈ 2.5 μg/disc) against Saccharomyces cerevisiae, similar to the positive control amphotericin B and ordinary activities (MIA ≈ 10 μg/disc) against Penicillium avellaneum UC-4376, Candida glabrata, Trichosporon beigelii and Pyricularia oryzae. Compound 2 is a better antifungal agent than compound 1 against most of the fungal strains that were tested.

Discovery of the chemical function of glycosidases: Design, synthesis, and evaluation of mass-differentiated carbohydrate libraries

Equation presented. Discovery of the catalytic chemical function of the many putative glycosidases coded in genomes currently relies on individual testing of possible substrates, usually as their p-nitrophenol conjugate. Herein, we present an alternative chemical proteomics approach using a synthetic mass-differentiated heat-stable substrate library with mass spectrometry readout. Library components do not serve as reaction inhibitors and both primary and secondary enzyme substrates can be delineated.

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.

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.