3945-18-4

Basic information

• Product Name: 3,4-DI-O-ACETYL-L-ARABINAL
• Synonyms: 3,4-DI-O-ACETYL-L-ARABINAL;3,4-Di-O-acetyl-L-arabinal,97%
• CAS NO: 3945-18-4
• Molecular Formula: C₉H₁₂O₅
• Molecular Weight: 200.19
• Mol File: 3945-18-4.mol

Chemical Properties

• Boiling Point: 266.2 °C at 760 mmHg
• Flash Point: 112.8 °C
• Appearance: Clear colorless to yellow/Oil
• Density: 1.2 g/cm³
• Vapor Pressure: 0.00878mmHg at 25°C
• Refractive Index: 1.458-1.46
• CAS DataBase Reference: 3,4-DI-O-ACETYL-L-ARABINAL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DI-O-ACETYL-L-ARABINAL(3945-18-4)
• EPA Substance Registry System: 3,4-DI-O-ACETYL-L-ARABINAL(3945-18-4)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 3945-18-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H12O5/c1-6(10)13-8-3-4-12-5-9(8)14-7(2)11/h3-4,8-9H,5H2,1-2H3/t8-,9+/m1/s1

Upstream product

• 3068-29-9 2,3,4-tri-O-acetyl-β-D-arabinosyl bromide 
• 108-24-7 acetic anhydride 
• 100897-60-7 2,3,4-Tri-O-acetyl-α-D-arabino-pyranosyl chloride 
• 39524-37-3 (2R,3S,4R,5R)-2-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 107-13-1 acrylonitrile 
• 4258-01-9 1,3,4-tri-O-acetyl-2-deoxy-β-D-erythro-pentopyranose 
• 14227-90-8 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide 
• 51830-02-5 bromo-2,3,4-O-triacetyl-α/β-L-arabinopyranoside 
• 87-72-9 L-(+)-arabinose 
• 28697-53-2 D-arabinopyranose 
• 108646-05-5 (3S,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 
• 39524-39-5 2,3,4-tri-O-acetyl-α-D-ribopyranosyl bromide 
• 50730-32-0 2,3,5-tri-O-acetyl-D-ribopyranosyl bromide 
• 5328-37-0 L-arabinose 

Downstream Products

• 88377-44-0 α-(4'-O-Acetyl-2',3'-dideoxy-α-D-glycero-pent-2'-enopyranosyl)acetophenone 
• 23914-43-4 2,2',4,4',6,6'-Hexachlor-azobenzen 
• 1213263-96-7 C₁₆H₁₄O₄ 
• 72946-54-4 1-(5-acetoxy-5,6-dihydro-2H-pyran-2-yl)-4-benzoylamino-1H-pyrimidin-2-one 
• 81666-71-9 4-Amino-1-((2R,5R)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl)-1H-pyrimidin-2-one 
• 123-76-2 levulinic acid 
• 864277-16-7 Acetic acid (3R,6R)-6-(2-benzyloxymethyl-allyl)-3,6-dihydro-2H-pyran-3-yl ester 

Relevant articles and documents

Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement

Stereoselective glycosylation is challenging in carbohydrate chemistry. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside and α-sulfoxide-glucoside, respectively.

Synthesis of xylal- and arabinal-based crown ethers and their application as asymmetric phase transfer catalysts

New xylal- and arabinal-based monoaza-15-crown-5 ethers were synthesized starting from l- and d-xylose, and l- and d-arabinose, respectively. These monosaccharide-based chiral macrocycles were tested as phase transfer catalysts in a few asymmetric reactions. The xylal-based crown compounds proved to be efficient catalysts in a few liquid-liquid phase reactions. The epoxidation of trans-chalcone and the Darzens condensation of α-chloroacetophenone with benzaldehyde took place with complete diastereoselectivity and up to 77% ee and 58% ee, respectively. It was found that the substituents in the aromatic ring of the chalcone and the α-chloroacetophenone had an influence on the enantioselectivity. The highest ee values were obtained in the epoxidation of 4-chlorochalcone (81% ee) and in the reaction of a 2-naphthyl analogue (96% ee), while in the Darzens condensation of 4-phenyl-α-chloroacetophenone with benzaldehyde, a maximum ee of 91% was detected. The configuration of the monosaccharide unit in the crown ring influenced the absolute configuration of the epoxyketones synthesized.

Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors

Lysophosphatidylserine (LysoPS), an endogenous ligand of G protein-coupled receptors, consists of l-serine, glycerol, and fatty acid moieties connected by phosphodiester and ester linkages, respectively. An ester linkage of phosphatidylserine can be hydrolyzed at the 1-position or at the 2-position to give 2-acyl lysophospholipid or 1-acyl lysophospholipid, respectively. 2-Acyl lysophospholipid is in nonenzymatic equilibrium with 1-acyl lysophospholipid in vivo. On the other hand, 3-acyl lysophospholipid is not found, at least in mammals, raising the question of whether the reason for this might be that the 3-acyl isomer lacks the biological activities of the other isomers. Here, to test this idea, we designed and synthesized a series of new 3-acyl lysophospholipids. Structure-activity relationship studies of more than 100 "glycol surrogate"derivatives led to the identification of potent and selective agonists for LysoPS receptors GPR34 and P2Y10. Thus, the non-natural 3-acyl compounds are indeed active and appear to be biologically orthogonal with respect to the physiologically relevant 1-and 2-acyl lysophospholipids.

THERAPEUTIC COMPOUNDS

The invention provides compounds of formula (I): and salts thereof, wherein R1, R2, R3, B, X, Y, and Z have any of the values defined herein. The invention also provides pharmaceutical compositions comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof, processes for preparing compounds of formula (I) and salts thereof, intermediates useful for preparing compounds of formula (I) and salts thereof, and therapeutic methods for treating cancer using a compound of formula (I) or a pharmaceutically acceptable salt thereof.

Preparation method of glycal

The invention belongs to the technical field of chemical engineering and discloses a preparation method of glycal. The method comprises the following steps: (1) adding an organic solvent into a reactor equipped with polyhydroxyaldehyde monosaccharide and a catalyst in an atmosphere of nitrogen, adding a hydroxyl protective agent, carrying out a reflux reaction, and carrying out subsequent processing to obtain a compound a; (2) successively adding ammonium salt and an organic solvent into the compound a under the condition of nitrogen so as to carry out a reaction, and carrying out subsequent processing to obtain a compound b; (3) letting the compound b, substituted hydrazine and a water-removal additive into an organic solvent under the condition of nitrogen so as to carry out a reaction, and carrying out subsequent processing to obtain a compound c; and (4) adding a catalyst and the compound c dissolved in the organic solvent into alkali under the condition of nitrogen, reacting, and carrying out subsequent processing so as to obtain glycal. The preparation method is simple and easy to operate, is low-cost and environment-friendly, and has market advantages. Meanwhile, yield of glycal prepared by the preparation method is good.

2,3-b deoxyribose and 2,3-dideoxy -2,3-didehydro-ribose and its precursor compound preparation method

The invention relates to a preparation method for preparing a precursor compound of 2, 3-dideoxyribose and 2, 3-dideoxy-2, 3-didehydroribose and a preparation method for preparing the 2, 3-dideoxyribose and the 2, 3-dideoxy-2, 3-didehydroribose through the precursor compound. The precursor compound is acetal with the structure as shown in formula (3). The method is characterized by comprising the following steps of: 1) enabling glucal with the structure as shown in formula (1) to be in contact with an alcohol under Ferrier reaction conditions in the presence of an acid to obtain 2, 3-dideoxy-2, 3-didehydroglycoside with the structure as shown in formula (2); and enabling the 2, 3-dideoxy-2, 3-didehydroglycoside with the structure as shown in formula (2) to be in contact with an alkaline compound in the presence of a solvent to obtain glycoside with the structure as shown in formula (3). The preparation method of the precursor compound, the 2, 3-dideoxyribose and the 2, 3-dideoxy-2, 3-didehydroribose, provided by the invention, has the advantages of simple steps, low cost and high yield.

An efficient method for the synthesis of pyranoid glycals

A simple and efficient procedure was designed for the preparation of pyranoid glycals. In a novel fashion, a series of protected glycopyranosyl bromides underwent reductive elimination in the presence of zinc dust and ammonium chloride in CH3CN at 30-60 °C. The corresponding glycals were obtained with excellent isolated yields (72-96%) in a short time (20-50 min). Furthermore, the transformation was compatible with different protection patterns and conveniently scalable (86% for 45 g acetobromoglucose) which made it very applicable in organic synthesis.

1 -(CYCLOPENT-2-EN-1 -YL)-3-(2-HYDROXY-3-(ARYLSULFONYL)PHENYL)UREA DERIVATIVES AS CXCR2 INHIBITORS

The invention relates to 1-(3-sulfonylphenyl)-3-(cyclopent-2-en-1-yl)urea derivatives, and their use in treating or preventing diseases and conditions mediated by the CXCR2 receptor. In addition, the invention relates to compositions containing the derivatives and processes for their preparation.

A rapid synthesis of pyranoid glycals promoted by β-cyclodextrin and ultrasound

A convenient and environmentally benign procedure for the synthesis of glycals from glycosyl bromides with very low zinc dust loading (1.5 equiv.) is described. The process is activated by β-cyclodextrin and ultrasound. Based on 19 samples, this method has been demonstrated to be highly effective for a broad range of glycosyl bromides, including acid- or base-sensitive and disaccharide glycosyl bromides. A yield of 85%-96% of glycals was obtained. Copyright

A simple and convenient method for the synthesis of pyranoid glycals

A simple, mild, and environmentally benign synthesis procedure of pyranoid glycals is described. In a novel fashion, protected glycopyranosyl bromides undergo the reductive elimination in the presence of zinc in phosphate buffer at room temperature. The pyranoid glycals were obtained in good-to-excellent yields (18 examples).