144490-03-9

Basic information

• Product Name: 1,2,3,5-TETRA-O-ACETYL-BETA-L-RIBOFURANOSE
• Synonyms: BETA-L-RIBOFURANOSE TETRAACETATE;1,2,3,5-TETRA-O-ACETYL-B-L-RIBOFURANOSE;1,2,3,5-TETRA-O-ACETYL-BETA-L-RIBOFURANOSE;1,2,3,5-Tetra-O-acectyl-beta-L-ribofuranose;β-l-ribofuranose 1,2,3,5-tetra-o-acetate;1,2,4,6-TETRA-O-ACETYL-BETA-L-RIBOFURANOSE;Tetraacetyl-L-Ribose;1,2,3,5-Tetra-O-acetyl-β-L-ribofuranose ,98%
• CAS NO: 144490-03-9
• Molecular Formula: C₁₃H₁₈O₉
• Molecular Weight: 318.28
• Mol File: 144490-03-9.mol

Chemical Properties

• Melting Point: 80-83 °C
• Boiling Point: 385.6±42.0 °C(Predicted)
• Appearance: White to Off-white/Powder
• Density: 1.29±0.1 g/cm3(Predicted)
• Refractive Index: 1.514
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Methanol (Slightly), Pyridine (Slightly)
• CAS DataBase Reference: 1,2,3,5-TETRA-O-ACETYL-BETA-L-RIBOFURANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,5-TETRA-O-ACETYL-BETA-L-RIBOFURANOSE(144490-03-9)
• EPA Substance Registry System: 1,2,3,5-TETRA-O-ACETYL-BETA-L-RIBOFURANOSE(144490-03-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 144490-03-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,2,3,5-TETRA-O-ACETYL-BETA-L-RIBOFURANOSE is used as a key intermediate in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine. This synthesis is crucial for the development of potential therapeutic agents and contributes to the advancement of pharmaceutical research.
Used in Chemical Synthesis:
As a white solid with unique chemical properties, 1,2,3,5-TETRA-O-ACETYL-BETA-L-RIBOFURANOSE can be utilized in various chemical synthesis processes, particularly for the creation of complex organic molecules and compounds. Its versatility in chemical reactions makes it a valuable component in the field of organic chemistry.

InChI:InChI=1/C13H18O9/c1-6(15)11(20)13(8(3)17,22-9(4)18)12(21,7(2)16)10(19)5-14/h10,14,19,21H,5H2,1-4H3/t10-,12-,13+/m0/s1

Upstream product

• 87-72-9 L-(+)-arabinose 
• 108-24-7 acetic anhydride 
• 5328-37-0 L-arabinose 
• 851367-08-3 methyl 2,3,6-tri-O-acetyl-5-deoxy-L-arabino-hexofuranoside 
• 1355330-54-9 1,2,3,5-tetra-O-tert-butyldimethylsilyl-α-L-arabinofuranose 
• 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 
• 10323-20-3 D-Arabinose 
• 108-05-4 vinyl acetate 
• 90244-44-3 methyl 2,3,5-tri-O-acetyl-α,β-D-arabinofuranoside 
• 41546-21-8 L-ribose 

Downstream Products

• 176299-73-3 5,6-dichloro-1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)benzimidazole 
• 390824-34-7 9-(2',3',5'-tri-O-acetyl-β-L-ribofuranosyl)-6-N-benzoyladenine 
• 390824-35-8 N²-acetyl-9-(2',3',5'-tri-O-acetyl-β-L-ribofuranosyl)-6-O-diphenylcarbamoylguanine 
• 461666-78-4 Acetic acid (2S,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-furan-3-yl ester 
• 461666-79-5 4'-methoxyphenyl α-L-arabinofuranoside 
• 461666-80-8 Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(4-methoxy-phenoxy)-tetrahydro-furan-2-ylmethoxy]-tetrahydro-furan-3-yl ester 
• 461666-81-9 Acetic acid (2S,3S,4R,5S)-4-acetoxy-2-((2R,3R,4S,5S)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxymethyl)-5-(4-methoxy-phenoxy)-tetrahydro-furan-3-yl ester 
• 328046-73-7 (R)-2-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethanol 
• 328046-71-5 ethyl 5-O-(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 
• 328046-72-6 ethyl 5-O-(2',3',5'-tri-O-benzyl-α-D-arabinofuranosyl)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-galactofuranoside 
• 328046-75-9 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 
• 328046-74-8 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 
• 206269-27-4 ribavirin 

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 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.

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.

Reaction kinetics and mechanism of sulfuric acid-catalyzed acetolysis of acylated methyl l-ribofuranosides

The mechanism of the sulfuric acid-catalyzed acetolysis of methyl 2,3,5-tri-O-acetyl- and methyl 2,3,5-tri-O-benzoyl-Lribofuranosides and the accompanying anomerization of both the starting material and the 1,2,3,5-tetra-O-acetyl- and 1-O-acetyl-2,3,5-tri-O-benzoyl-L-ribofuranoses formed was investigated. The progress of the reactions was followed by 1H NMR spectroscopy and the rate constants for the reactions were determined for a proposed kinetic model. The role of H+ and Ac + as the catalytically active species was clarified, proving that the anomerization of the acylated methyl furanosides is activated by protonation, while, on the contrary, the anomerization of the 1-O-acetyl ribofuranoses is activated by the acetyl cation. The anomerization of the acylated methyl furanosides was verified to be activated on the ring oxygen leading to endocyclic CO-bond rupture while the 1O-acetyl ribofuranoses are activated on the acetyloxy group on C(1) leading to exocyclic cleavage.

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.

METHOD FOR PRODUCTION OF FURANOSE DERIVATIVE

An object of the present invention is to provide a industrially appropriate method for producing the β-anomers of ribofuranose derivatives in a highly selective manner at a high yield. The present invention provides a method for producing ribofuranose derivatives wherein β-anomers is precipitated from among the generated furanose derivatives by controlling the amount of a reaction reagent used and/or using a poor solvent in the acetolysis reactions of 2,3,5-tri-O-acyl-1-O-alkyl-ribofuranose and 2,3-di-O-acyl-1-O-alkyl-5-deoxy-ribofuranose.

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

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.