61248-15-5

Basic information

• Product Name: 1,2,3,5-tetra-O-acetyl-α-D-xylofuranose
• Synonyms: 1,2,3,5-tetra-O-acetyl-α-D-xylofuranose
• CAS NO: 61248-15-5
• Molecular Weight: 318.281
• Mol File: 61248-15-5.mol

Chemical Properties

• CAS DataBase Reference: 1,2,3,5-tetra-O-acetyl-α-D-xylofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,5-tetra-O-acetyl-α-D-xylofuranose(61248-15-5)
• EPA Substance Registry System: 1,2,3,5-tetra-O-acetyl-α-D-xylofuranose(61248-15-5)

Safety Data

• Hazardous Substances Data: 61248-15-5(Hazardous Substances Data)

Upstream product

• 87-72-9 L-(+)-arabinose 
• 108-24-7 acetic anhydride 
• 10323-20-3 D-Arabinose 
• 532-20-7 D-arabinofuranose 
• 32453-58-0 methyl-2,3,4-tri-O-acetyl-6-deoxy-β-L-glucopyranoside 
• 28697-53-2 D-arabinopyranose 
• 67-56-1 methanol 
• 90244-44-3 methyl 2,3,5-tri-O-acetyl-α,β-D-arabinofuranoside 
• 32453-59-1 (2R,3S,4R,5R)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 87-72-9 D-Xylose 
• 58-86-6 D-xylose 
• 5328-37-0 L-arabinose 
• 1355330-54-9 1,2,3,5-tetra-O-tert-butyldimethylsilyl-α-L-arabinofuranose 
• 851367-08-3 methyl 2,3,6-tri-O-acetyl-5-deoxy-L-arabino-hexofuranoside 

Downstream Products

• 461666-78-4 Acetic acid (2S,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-furan-3-yl ester 
• 106824-96-8 2-β-D-ribofuranosyl-4-chloro-5-methoxycarbonyl-1,2,3-triazole 
• 402758-82-1 methyl 2-O-benzyl-α-D-arabinofuranoside 
• 917590-96-6 p-tolyl 2-O-benzyl-3,5-O-(tetraisopropylsiloxane-1,3-diyl)-1-thio-α-D-arabinofuranoside 
• 367274-96-2 p-cresyl 2-O-benzyl-1-thio-α-D-arabinofuranoside 
• 204918-57-0 (2R,3S,3aS,9aR)-5,5,7,7-Tetraisopropyl-2-p-tolylsulfanyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol 
• 204918-49-0 p-methylphenyl 1-thio-α-D-arabinofuranoside 
• 932719-69-2 methyl 2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-α-D-arabinofuranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 932719-13-6 p-tolyl 2-O-benzyl-3,5-O-(di-tert-butylsilanediyl)-1-thio-α-D-arabinofuranoside 

Relevant articles and documents

A Synthesis Strategy for the Production of a Macrolactone of Gulmirecin A via a Ni(0)-Mediated Reductive Cyclization Reaction

A synthesis strategy for the production of a key synthetic intermediate of gulmirecin A was described. The key reaction in the preparation of the 12-membered macrolactone is the Ni(0)-mediated reductive cyclization reaction of ynal using an N-heterocyclic carbene ligand and silane reductant. In addition, the α-selective glycosylation reaction of the macrolactone was performed to demonstrate the synthesis of gulmirecin and disciformycin precursors.

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.

Two-step synthesis of per-O-acetylfuranoses: Optimization and rationalization

A simple two-step procedure yielding peracetylated furanoses directly from free aldoses was implemented. Key steps of the method are (i) highly selective formation of per-O-(tert-butyldimethylsilyl)furanoses and (ii) their clean conversion into acetyl ones without isomerization. This approach was easily applied to galactose and structurally related carbohydrates such as arabinose, fucose, methyl galacturonate and N-acetylgalactosamine to give the corresponding peracetylated targets. The success of this procedure relied on the control of at least three parameters: (i) the tautomeric equilibrium of the starting unprotected oses, (ii) the steric hindrance of both targeted furanoses and silylating agent, and finally, (iii) the reactivity of each soft nucleophile during the protecting group interconversion.

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.

Synthesis of a dimer of β-(1,4)-l-arabinosyl-(2 S,4 R)-4-hydroxyproline inspired by art v 1, the major allergen of mugwort

Nα-tert-Butoxycarbonyl-l-trans-4-hydroxyproline allyl ester (Boc-Hyp-OAll) was glycosylated with 2,3,5-tri-O-benzyl-l-arabinose p-cresylthioglycoside in 60% yield with 4:1 β:α stereoselectivity. Deprotection of N- and C-terminii independently gave a prolyl amine and prolyl carboxylate respectively that were coupled under standard conditions with 1-[bis-(dimethylamino)methylene]-1H-1,2,3-triazolo-[4,5,b]-pyridininium hexafluorophosphate 3-oxide (N-HATU) to give the dimer 1 in 46% yield. These results represent the first steps toward the production of homogeneous oligomers to determine the minimal epitope of the Art v 1 allergen.

Diastereoselective enzymatic preparation of acetylated pentofuranosides carrying free 5-hydroxyl groups

Methyl 3-O-acetyl-2-deoxy-α-d-ribofuranoside, 1,3-di-O-acetyl-2-deoxy-α-d-ribofuranose and 1,2,3-tri-O-acetyl-α-d-arabinofuranose were diastereoselectively prepared (de = 100%) from anomeric mixtures of the corresponding 5-acetylated compounds through Can

Studies toward the total synthesis of carba analogue of motif C of M. TB cell wall AG complex

Herein we describe the synthesis of the carba analogue of motif C of arabinogalactan complex present in M. tuberculosis cell wall. Pd(0) catalyzed allylic alkylation and Fraser-Reid's glycosidation are the two key reactions that were employed for the synthesis of central glycosyl accepter unit and the glycosylation respectively.

Vinyl acetate and sodium carbonate as a fast and efficient catalyst for per-O-acetylation of monosaccharides

Vinyl acetate and sodium carbonate catalysed acetylation of several monosaccharides is an efficient synthesis of per-O-acetylation of carbohydrates and achieve the products in excellent yields and short reaction times. D-Glucose as the substrate in large scale also proceeds in high yield.

On the use of 3,5-O-benzylidene and 3,5-O-(Di-tert-butylsilylene)-2-O- benzylarabinothiofuranosides and their sulfoxides as glycosyl donors for the synthesis of β-arabinofuranosides: Importance of the activation method

A 2-O-benzyl-3,5-O-benzylidene-α-D-thioarabinofuranoside was obtained by reaction of the corresponding diol with α,α-dibromotoluene under basic conditions. On activation with 1-benzenesulfinyl piperidine, or diphenyl sulfoxide, and trifluoromethanesulfonic anhydride in dichloromethane at -55 °C, reaction with glycosyl acceptors affords anomeric mixtures with little or no selectivity. The analogous 2-O-benzyl-3,5-O-(di-tert-butylsilylene)- α-D-thioarabinofuranoside also showed no significant selectivity under the 1-benzenesulfinyl piperidine or diphenyl sulfoxide conditions. With N-iodosuccinimide and silver trifluoromethanesulfonate the silylene acetal showed moderate to high β-selectivity, independent of the configuration of the starting thioglycoside. High β-selectivity was also obtained with a 2-O-benzyl-3,5-O-(di-tert-butylsilylene)-α-arabinofuranosyl sulfoxide donor on activation with trifluoromethanesulfonic anhydride. The high β-selectivities obtained by the N-iodosuccinimide/silver trifluoromethanesulfonate and sulfoxide methods are consistent with a common intermediate, most likely to be the oxacarbenium ion. The poor selectivity observed on activation of the thioglycosides with the 1-benzenesulfinyl piperidine, or diphenyl sulfoxide, and trifluoromethanesulfonic anhydride methods appears to be the result of the formation of a complex mixture of glycosyl donors, as determined by low-temperature NMR work.

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