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
• Article Data: 26

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

Description

1,2,3,5-TETRA-O-ACETYL-BETA-L-RIBOFURANOSE is a white solid chemical compound that is an isomer of 1,2,3,5-TETRA-O-ACETYL-BETA-D-RIBOFURANOSE (T283100). It plays a significant role in the synthesis of various chemical compounds, particularly in the field of pharmaceuticals.

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

• 67-56-1 methanol 
• 532-20-7 D-arabinofuranose 
• 108-24-7 acetic anhydride 
• 162491-62-5 (2S,3R,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol 
• 41546-21-8 L-ribose 
• 659722-56-2 methyl 2,3,5-tri-O-acetyl-β/α-L-ribofuranoside 
• 52689-56-2 methyl β-L-ribofuranoside 
• 659722-55-1 1,2,3,5-tetra-O-acetyl-α-L-ribofuranose 
• 1202190-16-6 1,2,3,4,5-penta-O-acetyl-L-ribose methyl hemiacetal 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 
• 206269-25-2 methyl 2,3,5-tri-O-acetyl-β-L-ribofuranoside 
• 176299-71-1 1,2,3,5-tetraacetyl-L-ribofuranose 
• 390824-25-6 1,5-di-O-acetyl-3-O-benzyl-2-O-methanesulfonyl-L-arabinofuranose 

Downstream Products

• 58-96-8 L-uridine 
• 31501-46-9 (2S,3S,3aR,9aS)-3-hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2,3’:4,5]oxazolo[3,2-a]pyrimidin-6-one 
• 1439372-84-5 (1R,2S,3R,5R,8aR)-2-(benzyloxy)-3-(benzyloxymethyl)-5-methyl-1,2,3,5,6,8a-hexahydroindolizin-1-ol 
• 1439372-93-6 (2R,3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-1-(but-3-enyl)-2-styrylpyrrolidin-3-ol 
• 1439372-82-3 (2R,3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-1-((R)-pent-4-en-2-yl)-2-styrylpyrrolidin-3-ol 
• 1439372-89-0 (2S,3R,4R,E)-1,3-bis(benzyloxy)-5-(but-3-enylamino)-7-phenylhept-6-ene-2,4-diol 
• 1439372-80-1 (2S,3R,4R,E)-1,3-bis(benzyloxy)-5-((R)-pent-4-en-2-ylamino)-7-phenylhept-6-ene-2,4-diol 
• 320592-10-7 (3aS,5S,6S,6aS)-6-(benzyloxy)-5-(benzyloxymethyl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxole 
• 1439372-97-0 (1R,2S,3R,8aR)-2-(benzyloxy)-3-(benzyloxymethyl)-1,2,3,5,6,8a-hexahydroindolizin-1-ol 
• 268566-59-2 5,6-dichloro-1-[2-phenoxythionoformyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)-β-L-ribofuranosyl]benzimidazole 
• 263708-22-1 1-[2-O-phenylthioformate-3,5-O-(1,1,3,3-tetraisopropyl-1,3-O-disiloxanyl)-β-L-ribofuranosyl]-1,2,4-triazole-3-carboxamide 
• 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.

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.