18469-06-2

Basic information

• Product Name: .beta.-D-Allopyranoside, methyl
• Synonyms: .beta.-D-Allopyranoside, methyl
• CAS NO: 18469-06-2
• Molecular Formula: C₇H₁₄O₆
• Molecular Weight: 0
• Mol File: 18469-06-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: .beta.-D-Allopyranoside, methyl(CAS DataBase Reference)
• NIST Chemistry Reference: .beta.-D-Allopyranoside, methyl(18469-06-2)
• EPA Substance Registry System: .beta.-D-Allopyranoside, methyl(18469-06-2)

Safety Data

• Hazardous Substances Data: 18469-06-2(Hazardous Substances Data)

Upstream product

• 2460-42-6 methyl-β-D-ribo-hexapyranoside-3-ulose 
• 7732-18-5 water 
• 64-17-5 ethanol 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 22277-65-2 Methyl mannoside 
• 709-50-2 methyl beta-D-glucopyranoside 
• 18276-53-4 1-(trimethylsilyl)-1H-pyrrole 
• 110744-71-3 acanthacerebroside A 
• 67-56-1 methanol 
• 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 
• 112670-18-5 hexahydro OP-I(U) 
• 34367-04-9 chikusetsusaponin V 
• 79431-99-5 13-O-<β-maltosyl(1->2)-β-D-glucosyl>-19-O-β-D-glucosyl-steviol 

Downstream Products

• 116498-86-3 methyl 2,3:4,6-di-O-benzylidene-β-D-allopyranoside 
• 114244-88-1 methyl 6-O-benzoyl-β-D-allopyranoside 
• 324530-37-2 2,3,4,6-Tetra-O-benzyl-methyl-α/β-D-galactopyranoside 
• 103368-01-0 2,3,4,6-tetra-O-benzyl-α-L-mannopyranose 1-O-trichloroacetimidate 
• 103368-04-3 2,3,4,6-tetra-O-benzyl-β-L-mannopyranose 1-O-trichloroacetimidate 
• 604-70-6 tetra-O-acetyl-1-O-methyl-β-D-glucopyranose 
• 15830-76-9 methyl 2,3,4-tri-O-acetyl-6-deoxy-α-D-talopyranoside 
• 4860-85-9 methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 6605-40-9 methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 32849-03-9 methyl 2,3,4,6-tetra-O-benzoyl-α-D-glycopyranoside 
• 84799-77-9 methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 1333212-93-3 (25R)-3β,16β-diacetoxy-22-oxocholest-5-en-26-yl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 

Relevant articles and documents

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).

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.

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.

Catalytic glycosylation of glucose with alkyl alcohols over sulfonated mesoporous carbons

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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.

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

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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.

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.

Kinetic analysis of hexose conversion to methyl lactate by Sn-Beta: Effects of substrate masking and of water

Simple sugars show promise as substrates for the formation of fuels and chemicals using heterogeneous catalysts in alcoholic solvents. Sn-Beta is a particularly well-suited catalyst for the cleavage, isomerization and dehydration of sugars into more valuable chemicals. In order to understand these processes and save resources and time by optimising them, kinetic and mechanistic analyses are helpful. Herein, we study substrate entry into the Sn-Beta-catalysed methyl lactate process using abundant hexose substrates. NMR spectroscopy is applied to show that the formation of methyl lactate occurs in two kinetic regimes for fructose, glucose and sucrose. The majority of methyl lactate is not formed from the substrate directly, but from methyl fructosides in a slow regime. At 160 °C, more than 40% of substrate carbon are masked (i.e. reversibly protected in situ) as methyl fructosides within a few minutes when using hydrothermally synthesised Sn-Beta, while more than 60% methyl fructosides can be produced within a few minutes using post-synthetically treated Sn-Beta. A significant fraction of the substrate is thus masked by rapid methyl fructoside formation prior to subsequent slow release of fructose. This release is the rate-limiting step in the Sn-Beta-catalysed methyl lactate process, but it can be accelerated by the addition of small amounts of water at the expense of the maximum methyl lactate yield.