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beta-D-Ribofuranose 1,2,3,5-tetraacetate

CAS No.13035-61-5
Chemical Name:beta-D-Ribofuranose 1,2,3,5-tetraacetate
CBNumber:CB4682585
Molecular Formula:C13H18O9
Formula Weight:318.28
MOL File:13035-61-5.mol

beta-D-Ribofuranose 1,2,3,5-tetraacetate Property

Melting point 81-83 °C(lit.)
alpha -15.4 º (c=7, MeOH)
Boiling point 417.45°C (rough estimate)
Density 1.4171 (rough estimate)
refractive index -14.5 ° (C=5, MeOH)
storage temp. Inert atmosphere,Room Temperature
solubility Chloroform (Sparingly), Methanol (Slightly)
form Crystalline Powder
color White to almost white
optical activity [α]26/D 11.4°, c = 10 in chloroform
BRN 94078
InChI InChI=1/C13H18O9/c1-6(14)18-5-10-11(19-7(2)15)12(20-8(3)16)13(22-10)21-9(4)17/h10-13H,5H2,1-4H3/t10-,11-,12-,13-/s3
InChIKey TTXVPMATRDJQIA-BKUVIOGVSA-N
SMILES [C@@H]1(OC(=O)C)[C@@H](COC(=O)C)O[C@@H](OC(=O)C)[C@@H]1OC(=O)C |&1:0,5,12,17,r|
CAS DataBase Reference 13035-61-5(CAS DataBase Reference)
UNSPSC Code 12352201
NACRES NA.22

Safety

Hazard Codes :Xi
Risk Statements :36/37/38
Safety Statements :22-24/25-36-26
WGK Germany :3
HS Code :29400090

NFPA 704:

	1
0		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H315-H319-H335
Precautionary statements P280-P261

beta-D-Ribofuranose 1,2,3,5-tetraacetate Price More Price(11)

Brand: Sigma-Aldrich(India)
Product number: 159026
Product name : β-D-Ribofuranose 1,2,3,5-tetraacetate
Purity: 98%
Packaging: 5G
Price: ₹2800
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 159026
Product name : β-D-Ribofuranose 1,2,3,5-tetraacetate
Purity: 98%
Packaging: 25G
Price: ₹10780
Updated: 2022/06/14
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Brand: ALFA India
Product number: ALF-B24426-22
Product name : beta-D-Ribofuranose 1,2,3,5-tetraacetate, 98+%
Purity:
Packaging: 100g
Price: ₹34257
Updated: 2022/05/26
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Brand: TCI Chemicals (India)
Product number: R0066
Product name : Tetra-O-acetyl-β-D-ribofuranose
Purity: min. 98.0 %
Packaging: 5G
Price: ₹2600
Updated: 2022/05/26
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Brand: TCI Chemicals (India)
Product number: R0066
Product name : Tetra-O-acetyl-β-D-ribofuranose
Purity: min. 98.0 %
Packaging: 25G
Price: ₹8200
Updated: 2022/05/26
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beta-D-Ribofuranose 1,2,3,5-tetraacetate Chemical Properties,Usage,Production

Description beta-D-Ribofuranose 1,2,3,5-tetraacetate is an acetylated derivative of ribose extensively used in carbohydrate research and synthetic chemistry. This compound features acetyl groups protecting the hydroxyl functionalities at positions 1, 2, 3, and 5 of the ribofuranose ring, which enhances its stability and solubility in organic solvents. β-D-Ribofuranose 1,2,3,5-tetraacetate is a crucial intermediate in synthesising nucleosides, nucleotides, and other complex carbohydrates. In research, it is utilized to study glycosylation mechanisms, focusing on the formation and stereochemistry of glycosidic bonds.
Chemical Properties beta-D-Ribofuranose 1,2,3,5-tetraacetate is white to almost white crystalline powder
Uses beta-D-Ribofuranose 1,2,3,5-tetraacetate 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.
Application beta-D-Ribofuranose 1,2,3,5-tetraacetate, also known as 1,2,3,5-tetra-O-Acetyl-beta-D-ribofuranose (TAR), is an important organic reagent that can be used in the following pathways:
(1) Used in low-energy electron-induced reactions in gas-phase TAR. Since the acetyl group in TAR is coupled to the five-membered ribose ring at relevant positions, it can serve as a suitable model compound for studying the reaction of sugar units in DNA to low-energy electrons[1].
(2) Used to prepare 1,2,3-tri-O-acetyl-β-d-ribofuranose by enzymatic deacetylation[2].
(3) Used in condensation reactions. In the presence of tin chloride, 1-hexene reacts with 1- O -acetyl-2,3,5-tri- O -benzoyl-β- d -ribofuranose ( 5b ) or 1,2,3,5-tetra- O -acetyl-β- d -ribofuranose ( 5a ) to form a complex mixture[3].
References [1] ILKO BALD. Low energy electron-induced reactions in gas phase 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose: a model system for the behavior of sugar in DNA.[J]. Journal of Chemical Physics, 2007. DOI:10.1063/1.2436873.
[2] TUN-CHENG CHIEN; Ji W C. A convenient preparation of 1,2,3-tri-O-acetyl-β-d-ribofuranose by enzymatic regioselective 5-O-deacetylation of the peracetylated ribofuranose[J]. Carbohydrate Research, 2004. DOI:10.1016/j.carres.2004.01.010.
[3] THOMAS L. CUPPS; Leroy B T; Dean S Wise. A further investigation of the stannic chloride-catalyzed condensation reaction of 1-hexene and 1,2,3,5-tetra-O-acyl-β-d-ribofuranoses[J]. Carbohydrate Research, 1983. DOI:10.1016/0008-6215(83)88135-X.