23094-61-3

Basic information

• Product Name: 1,2,3,5-tetra-O-acetyl-β-D-xylofuranose
• Synonyms: 1,2,3,5-tetra-O-acetyl-β-D-xylofuranose
• CAS NO: 23094-61-3
• Molecular Weight: 318.281
• Mol File: 23094-61-3.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: 1,2,3,5-tetra-O-acetyl-β-D-xylofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,5-tetra-O-acetyl-β-D-xylofuranose(23094-61-3)
• EPA Substance Registry System: 1,2,3,5-tetra-O-acetyl-β-D-xylofuranose(23094-61-3)

Safety Data

• Hazardous Substances Data: 23094-61-3(Hazardous Substances Data)

Upstream product

• 87-72-9 L-(+)-arabinose 
• 108-24-7 acetic anhydride 
• 1355330-54-9 1,2,3,5-tetra-O-tert-butyldimethylsilyl-α-L-arabinofuranose 
• 5328-37-0 L-arabinose 
• 58-86-6 D-xylose 
• 87-72-9 D-Xylose 
• 67-56-1 methanol 
• 532-20-7 D-arabinofuranose 
• 28697-53-2 D-arabinopyranose 
• 32453-59-1 (2R,3S,4R,5R)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 32453-58-0 methyl-2,3,4-tri-O-acetyl-6-deoxy-β-L-glucopyranoside 
• 90244-44-3 methyl 2,3,5-tri-O-acetyl-α,β-D-arabinofuranoside 
• 10323-20-3 D-Arabinose 
• 108-05-4 vinyl acetate 

Downstream Products

• 461666-78-4 Acetic acid (2S,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-furan-3-yl ester 
• 1027638-25-0 2-chloro-4-nitrophenyl 2,3,5-tri-O-acetyl-α-L-arabinofuranoside 
• 31079-96-6 O-monomethoxytrityl-5' β-D-xylofurannosyl-9 adenine 
• 15830-77-0 O²,O³,O⁵-triacetyl-1-(6-amino-purin-9-yl)-β-D-1-deoxy-xylofuranose 
• 1313588-82-7 4-(4-chlorophenyl)-2-(2',3',5'-tri-O-acetyl-β-D-xylofuranosyloxy)-6-(thien-2-yl)nicotinonitrile 
• 1153940-80-7 methyl 2,3,4-tri-O-benzoyl-6-S-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)-6-thio-α-D-glucopyranoside 
• 1153940-88-5 methyl 2,3,4-tri-O-benzoyl-6-S-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)-6-thio-α-D-galactoyranoside 
• 883732-46-5 N-benzoyl-2-(cyclopentyloxy)-9-(2,3,5-tri-O-acetyl-β-D-xylofuranosyl)-9H-purin-6-amine 
• 106824-96-8 2-β-D-ribofuranosyl-4-chloro-5-methoxycarbonyl-1,2,3-triazole 
• 328046-74-8 acetic acid 4-acetoxy-2-[2-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-(3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethoxy]-5-(1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester 
• 328046-75-9 ethyl 5-O-(2',3',5'-tri-O-benzyl-α-D-arabinofuranosyl)-6-O-(β-D-galactofuranosyl)-2,3-di-O-benzyl-β-D-galactofuranoside 
• 328046-72-6 ethyl 5-O-(2',3',5'-tri-O-benzyl-α-D-arabinofuranosyl)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-galactofuranoside 
• 328046-70-4 Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-1-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-tetrahydro-furan-3-yl ester 
• 328046-71-5 ethyl 5-O-(α-D-arabinofuranosyl)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-galactofuranoside 

Relevant articles and documents

The arabinofuranoside method, a convenient substitute of the fucofuranoside method for determining the absolute configuration of the secondary alcohols

As a simple substitute of the fucofuranoside method, a recently devised technique for determining the absolute configuration of secondary alcohols by 13C NMR, the arabinofuranoside method is proposed. Unlike fucose, the derivatizing agent arabi

Stereoselective acetylation of hemicellulosic C5-sugars

The stereoselective peracetylation of α-D-xylose (1) and α-L-arabinose (4) using a combination of triethylamine and acetic anhydride in the presence or absence of a catalytic amount of dimethylaminopyridine (DMAP) is described. The peracetylated D-xylose and L-arabinose alpha pyranose anomers 2α and 5α are obtained in 97% and 56% yields respectively. The peracetylated D-xylose beta pyranose anomer 2β is obtained in 71% yield through simple modification of the reaction conditions. Details regarding synthesis and isolation optimization studies under different conditions are presented below. The stereoselective peracetylation reactions disclosed here have been used to separate mixtures of D-xylose and L-arabinose as their peracetylated derivatives 2β and 5α in 47% and 42% yields and can provide pure pentoses after deacetylation.

Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases

Derivatives of 5-deoxy-β-d-galactofuranose (5-deoxy-α-l-arabino- hexofuranose) have been synthesized starting from d-galacturonic acid. The synthesis of methyl 5-deoxy-α-l-arabino-hexofuranoside (14α) was achieved by an efficient strategy previously optimized, involving a photoinduced electron transfer (PET) deoxygenation. Compound 14α was converted into per-O-acetyl-5-deoxy-α,β-l-arabino-hexofuranoside (16), an activated precursor for glycosylation reactions. The SnCl4-promoted glycosylation of 16 led to 4-nitrophenyl (19α), and 4-methylthiophenyl 5-deoxy-α-l-arabino-hexofuranosides (20α). The oxygenated analog 4-methylphenyl 1-thio-β-d-galactofuranoside (23β) was also prepared. The 5-deoxy galactofuranosides were evaluated as inhibitors or substrates of the exo-β-d-galactofuranosidase from Penicillium fellutanum, showing that the absence of HO-5 drastically diminishes the affinity for the protein.