beta-D-Ribofuranose 1,2,3,5-tetraacetate
- Product Name
- beta-D-Ribofuranose 1,2,3,5-tetraacetate
- CAS No.
- 13035-61-5
- Chemical Name
- beta-D-Ribofuranose 1,2,3,5-tetraacetate
- Synonyms
- (2S,3R,4R,5R)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate;TETRAACETYLRIBOFURANOSE;beta-D-Ribofuranose;1,2,3,5-Tetraacetate;TETRA-O-ACETYL-BETA-D-RIBOFURANOSE;1,2,3,5-tera-O-acetyl-beta-D-ribofuranose;1,2,3,5-TETRA-O-ACETYL-BETA-D-RIBOFURANOSE;[(2R,3R,4R,5S)-3,4,5-triacetoxytetrahydrofuran-2-yl]methyl acetate;TETRAACETYLRIBOSE;RIBOFURANOSE 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)
Safety
- Hazard Codes
- Xi
- Risk Statements
- 36/37/38
- Safety Statements
- 22-24/25-36-26
- WGK Germany
- 3
- HS Code
- 29400090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
N-Bromosuccinimide Price
- Product number
- 159026
- Product name
- β-D-Ribofuranose 1,2,3,5-tetraacetate
- Purity
- 98%
- Packaging
- 5g
- Price
- $46.2
- Updated
- 2024/03/01
- Product number
- 159026
- Product name
- β-D-Ribofuranose 1,2,3,5-tetraacetate
- Purity
- 98%
- Packaging
- 25g
- Price
- $119
- Updated
- 2024/03/01
- Product number
- R0066
- Product name
- Tetra-O-acetyl-beta-D-ribofuranose
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $34
- Updated
- 2024/03/01
- Product number
- R0066
- Product name
- Tetra-O-acetyl-beta-D-ribofuranose
- Purity
- >98.0%(GC)
- Packaging
- 25g
- Price
- $116
- Updated
- 2024/03/01
- Product number
- B24426
- Product name
- beta-D-Ribofuranose 1,2,3,5-tetraacetate, 98+%
- Packaging
- 5g
- Price
- $35.65
- Updated
- 2024/03/01
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.
beta-D-Ribofuranose 1,2,3,5-tetraacetate Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from beta-D-Ribofuranose 1,2,3,5-tetraacetate manufacturers
- Product
- Tetraacetylribofuranose 13035-61-5
- Price
- US $0.00/Kg
- Min. Order
- 1Kg
- Purity
- 98%
- Supply Ability
- 20Ton
- Release date
- 2024-11-29
- Product
- 1,2,3,5-tera-O-acetyl-beta-D-ribofuranose 13035-61-5
- Price
- US $0.00-0.00/Kg
- Min. Order
- 1Kg
- Purity
- 99%
- Supply Ability
- 20Ton
- Release date
- 2024-11-29
- Product
- beta-D-Ribofuranose 1,2,3,5-tetraacetate 13035-61-5
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10tons/month
- Release date
- 2021-07-19