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

Chemical Properties

White solid

Uses

1,2,3,5-Tetra-O-acetyl β-L-Ribofuranose is an isomer of 1,2,3,5-Tetra-O-acetyl β-D-Ribofuranose (T283100) which is used 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.

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 
• 28697-53-2 D-arabinopyranose 
• 90244-44-3 methyl 2,3,5-tri-O-acetyl-α,β-D-arabinofuranoside 
• 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 

Downstream Products

• 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 
• 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 
• 1027638-25-0 2-chloro-4-nitrophenyl 2,3,5-tri-O-acetyl-α-L-arabinofuranoside 
• 26879-47-0 1-(β-L-ribofuranosyl)thymine 
• 1463-10-1 5-Methyluridine 
• 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 

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 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.