72274-54-5

Basic information

• Product Name: methyl 6-deoxy-β-L-altropyranoside
• CAS NO: 72274-54-5
• Molecular Weight: 178.185
• Mol File: 72274-54-5.mol

Chemical Properties

• CAS DataBase Reference: methyl 6-deoxy-β-L-altropyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 6-deoxy-β-L-altropyranoside(72274-54-5)
• EPA Substance Registry System: methyl 6-deoxy-β-L-altropyranoside(72274-54-5)

Safety Data

• Hazardous Substances Data: 72274-54-5(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 2438-80-4 L-Fucose 
• 73-34-7 6-deoxy-L-galactose 
• 92418-38-7 (3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate 
• 73-34-7 D-Fucose 
• 150650-49-0 methyl 2,3-di-O-acetyl-4-O-benzoyl-6-deoxy-β-D-galactopyranoside 
• 71117-36-7 methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 
• 39981-26-5 methyl 6-deoxy-3,4-O-isopropylidene-β-D-galactopyranoside 
• 1226-39-7 p-nitrophenyl-β-D-fucopyranoside 
• 6189-71-5 α-D-fucose 
• 5155-46-4 methyl 6-deoxy-6-iodo-D-altroside 
• 1128-40-1 methyl β-L-fucopyranoside 
• 73-34-7 L-rhamnose 
• 107195-78-8 [(25S)-3β-hydroxyspirost-5-en-1β-yl] 2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-galactopyranoside 

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 
• 1399293-50-5 methyl 3-O-(3,5-difluorobenzensulfonyl)-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 
• 3615-37-0 D-Fucose 
• 42214-01-7 methyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 14133-63-2 methyl 2,3-O-isopropylidene-α-L-rhamnoside 

Relevant articles and documents

Four new oleanene derivatives from the sseeds of Astragalus complanatus

Four new methyl ester derivatives of oleanene glycosides (3-6) were isolated from the seeds of Astragalus complanatus R. BR. together with two known triterpene glycosides, astragaloside VIII methyl ester (1) and soyasaponin I methyl ester (2) after treatment with diazomethane during separation procedure. The structures of 3-6 were elucidated as 3-O-α-L-rhamnopyranosyl(1→2)-β-D-xylopyranosyl(1→2)-6-O-methy-β-D- glucuronopyranosyl-soyasapogenol B 22-O-β-D-glucopyranoside, 3-O-α-L-rhamnopyranosyl(1 →2)-β-D-galactopyranosyl(1→2)-6-O-methyl-β-D-glucuronopyranosyl-soy asapogenol B 22-O-β-D-glucopyranoside, 3-O-α-L-rhamnopyranosyl(1→2)-β-D-xylopyranosyl(1→2)-6-O-methyl-β-D -glucuronopyranosyl 3β,22β,24-trihydroxy-11-oxo-olean-12-ene and 3-O-α-L-rhamnopyranosyl (1→2)-β-D-galactopyranosyl(1→2)-6-O-methyl-β-D-glucuronopyranosyl 3β,22β,24-trihydroxy-11-oxo-olean-12-ene, respectively.

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.

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.

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

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.

Steroidal saponins from the roots of Smilax sp.: Structure and bioactivity

Phytochemical characterization of a commercial herb sample supplied as Smilax ornata Lem. (sarsaparilla) led to the isolation of five steroidal saponins, including two new furostanol saponins sarsaparilloside B (1) and sarsaparilloside C (2), whose structures were elucidated via a combination of multistage mass spectrometry (MSn), 1D and 2D NMR experiments, and chemical degradation. The previously unreported spectroscopic characterization of sarsaparilloside (3), Δ20(22)-sarsaparilloside (4), and parillin (5) is also provided. The antiproliferative activity of the isolated saponins was compared in six human cell lines derived from different tumor types and one of the structures (2) was particularly active against the HT29 colon tumor cell line.

Access to antigens related to anthrose using pivotal cyclic sulfite/sulfate intermediates

Anthrose is the upstream terminal unit of the tetrasaccharide side chain from a major glycoprotein of Bacillus anthracis exosporium and is part of important antigenic determinants. A novel entry to anthrose-containing antigens and precursors is described. The synthetic route, starting from d(+)-fucose, makes use of intermediates featuring a cyclic sulfite or sulfate function which serves successively as a protecting and a leaving group.