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
• Article Data: 29

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 
• 39524-37-3 (2R,3S,4R,5R)-2-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 14227-90-8 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide 
• 58-86-6 D-xylose 
• 108-24-7 acetic anhydride 
• 50730-32-0 2,3,5-tri-O-acetyl-D-ribopyranosyl bromide 
• 100897-60-7 2,3,4-Tri-O-acetyl-α-D-arabino-pyranosyl chloride 
• 5328-37-0 L-arabinose 
• 87-72-9 L-(+)-arabinose 
• 1233-03-0 1,2,3,4-tetra-O-acetyl-L-arabinopyranose 
• 75247-31-3 α-1-bromo-1-deoxy-2,3,4-tri-O-acetyl-L-arabinopyranose 
• 64-19-7 acetic acid 
• 51830-02-5 bromo-2,3,4-O-triacetyl-α/β-L-arabinopyranoside 
• 10323-20-3 D-Arabinose 

Downstream Products

• 864277-16-7 Acetic acid (3R,6R)-6-(2-benzyloxymethyl-allyl)-3,6-dihydro-2H-pyran-3-yl ester 
• 864277-18-9 acetic acid 6-[2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-propyl]-3,6-dihydro-2H-pyran-3-yl ester 
• 864277-17-8 Acetic acid (3R,6R)-6-(3-benzyloxy-2-hydroxy-2-hydroxymethyl-propyl)-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.

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.