3945-17-3

Basic information

• Product Name: 3,4-DI-O-ACETYL-D-ARABINAL
• Synonyms: 1,2-Dideoxy-D-erythro-pent-1-enopyranose Diacetate;1,5-Anhydro-2-deoxy-D-erythro-pent-1-enitol 3,4-diacetate;3,4-Di-O-acetyl-D-ribal;Di-O-acetyl-D-arabinal;3,4-DI-O-ACETYL-D-ARABINAL;3,4-DI-O-ACETYL-D-ARABINOSE;(3R)-3,4-Dihydro-2H-pyran-3β,4β-diol diacetate;(3R)-3β,4β-Diacetoxy-3,4-dihydro-2H-pyran
• CAS NO: 3945-17-3
• Molecular Formula: C₉H₁₂O₅
• Molecular Weight: 200.19
• Product Categories: Carbohydrates & Derivatives
• Mol File: 3945-17-3.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,4-DI-O-ACETYL-D-ARABINAL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DI-O-ACETYL-D-ARABINAL(3945-17-3)
• EPA Substance Registry System: 3,4-DI-O-ACETYL-D-ARABINAL(3945-17-3)

Safety Data

• Hazardous Substances Data: 3945-17-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Liquid

Uses

D-Di-O-acetylarabinal (cas# 3945-17-3) is a compound useful in organic synthesis.

Upstream product

• 107-13-1 acrylonitrile 
• 4258-01-9 1,3,4-tri-O-acetyl-2-deoxy-β-D-erythro-pentopyranose 
• 10323-20-3 D-Arabinose 
• 113889-50-2 (3S,4R,5R)-2-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 19186-37-9 1,2,3,4-tetra-O-acetyl-α-D-arabinopyranose 
• 28697-53-2 D-arabinopyranose 
• 4627-30-9 (3R,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 
• 4257-95-8 1,2,3,4-tri-O-acetyl-α-D-ribopyranose 
• 108646-05-5 (3S,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 
• 64-19-7 acetic acid 
• 39524-39-5 2,3,4-tri-O-acetyl-α-D-ribopyranosyl bromide 
• 39524-37-3 (2R,3S,4R,5R)-2-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 50730-32-0 2,3,5-tri-O-acetyl-D-ribopyranosyl bromide 
• 108-24-7 acetic anhydride 

Downstream Products

• 85620-84-4 1,5-anhydro-2,3-dideoxy-D-glycero-pent-2-enitol 
• 1581705-18-1 (1S,4S,5S)-4-(benzyloxy)-2,8-dioxabicyclo[3.3.1]non-6-ene 
• 1581705-17-0 2-[(3S,4R)-3-(benzyloxy)-3,4-dihydro-2H-pyran-4-yl]acetaldehyde 
• 1581705-16-9 vinyl 4-O-benzyl-2,3-dideoxy-α-D-arabino-2-enopyranoside 
• 1581705-15-8 2-phenylselenenylethyl 4-O-benzyl-2,3-dideoxy-β-D-arabino-2-enopyranoside 

Relevant articles and documents

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.

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.

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