ChemicalBook > CAS DataBase List > beta-D-Ribofuranose 1,2,3,5-tetraacetate

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
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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)
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Safety

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

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
159026
Product name
β-D-Ribofuranose 1,2,3,5-tetraacetate
Purity
98%
Packaging
5g
Price
$46.2
Updated
2024/03/01
Sigma-Aldrich
Product number
159026
Product name
β-D-Ribofuranose 1,2,3,5-tetraacetate
Purity
98%
Packaging
25g
Price
$119
Updated
2024/03/01
TCI Chemical
Product number
R0066
Product name
Tetra-O-acetyl-beta-D-ribofuranose
Purity
>98.0%(GC)
Packaging
5g
Price
$34
Updated
2024/03/01
TCI Chemical
Product number
R0066
Product name
Tetra-O-acetyl-beta-D-ribofuranose
Purity
>98.0%(GC)
Packaging
25g
Price
$116
Updated
2024/03/01
Alfa Aesar
Product number
B24426
Product name
beta-D-Ribofuranose 1,2,3,5-tetraacetate, 98+%
Packaging
5g
Price
$35.65
Updated
2024/03/01
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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.

beta-D-Ribofuranose 1,2,3,5-tetraacetate Preparation Products And Raw materials

Raw materials

Inosine

Preparation Products

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

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View Lastest Price from beta-D-Ribofuranose 1,2,3,5-tetraacetate manufacturers

Xinxiang Aurora Biotechnology Co.,Ltd.
Product
Tetraacetylribofuranose 13035-61-5
Price
US $0.00/Kg
Min. Order
1Kg
Purity
98%
Supply Ability
20Ton
Release date
2024-11-29
Xinxiang Aurora Biotechnology Co.,Ltd.
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
WUHAN FORTUNA CHEMICAL CO., LTD
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

13035-61-5, beta-D-Ribofuranose 1,2,3,5-tetraacetateRelated Search:

Acetylacetone Acetaminophen Tetraacetylethylenediamine Acetylsalicylic acid Acetylcholine Acetylspiramycin Ribonucleic acid Acetyl chloride Acetyl coenzyme A sodium salt N-Acetyl-L-cysteine beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate 1-O-Acetyl-2,3,5-tri-O-(4-chlorobenzoyl)-beta-D-ribofuranose 1-ACETYL-2,3,5-TRI-O-BENZOYL-B-L-RIBOFURANOSE TETRAACETYLRIBOFURANOSE ETHYL-BIS-(SODIUMTETRAZOYLAZO)ACETATE 1,2,3,5-Tetra-O-benzoyl-2C-methyl-D-ribofuranose ACETAMINOPHENOL BP/USP beta-D-Ribofuranose 1,2,3,5-tetraacetate

  • TETRAACETYLRIBOFURANOSE
  • TETRAACETYLRIBOSE
  • TETRAACETYL-BETA-D-RIBOFURANOSE
  • TETRA-O-ACETYL-B-D-RIBOFURANOSE
  • TETRA-O-ACETYL-BETA-D-RIBOFURANOSE
  • RIBOFURANOSE TETRAACETATE
  • 1,2,3,5-Tetra-O-acetyl-
  • 1,2,3,5-tera-O-acetyl-beta-D-ribofuranose
  • BETA-D-RIBOFURANOSE 1,2,3,5-TETRAACETATE
  • 1,2,3,5-TETRA-O-ACETYL-B-D-*RIBOFURANOSE
  • -D-RIBOFURANOSE 1,2,3,5-TETRAACETATE
  • β-D-Ribo
  • 1,2,3,5-Tetraacetylribofuranose
  • D-Ribose tetraacetate
  • Tetraacetyl-β-D-ribofuranose
  • beta-D-Ribofuranose 1,2,3,5-tetraacetate, 98+%
  • á-d-ribofuranose 1,2,3,5-tetraacetate
  • β-d-ribofuranose 1,2,3,5-tetra-o-acetate
  • 1,2,3,5-Tetra-O-Acety
  • 1,2,3,5-tetra-o-acetyl-á-d-ribofuranose
  • SS-D-RIBOFURANOSE 1,2,3,5-TETRAACETATE
  • β-D-Ribofuranose 1,2,3,5-tetraacetate, 98+%
  • 1,2,3,5-TETRA-O-ACETYL-SS-D-RIBOFURANOSE
  • (2S,3R,4R,5R)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate
  • 1,2,3,5-Tetra-O-acetyl-β-D-ribofuranose, Tetraacetylribose
  • 1,2,3,5-Tetraacetyl-β-D-ribose
  • [(2R,3R,4R,5S)-4,5-Diacetyloxy-2-(acetyloxymethyl)oxolan-3-yl] acetate
  • Acetyl 2-O,3-O,5-O-triacetyl-β-D-ribofuranoside
  • ^b-D-Ribofuranose 1,2,3,5-tetraacetate, 98+%
  • 1-B-D-Ribofluranose-1,2,3,5-Tetraacetate
  • BETA-D-RIBOFURANOSE 1,2,3,5-TETRA-O-ACETATE
  • BETA-D-RIBOFURANOSE TETRAACETATE
  • BETA(R)-D-TETRAACETYL RIBOSE
  • 1,2,3,5-tetraacetyl-beta-d-furanoribose
  • 1,2,3,5-Tetraacetyl-beta-D-ribose
  • 1,2,3,5-TETRA-O-ACETYL-BETA-D-RIBOFURANOSE
  • 1,2,3,5-Tetra-O-acetyl-D-ribofuranose
  • 1,2,3,5-TETRAACETYL-B-D-RIBOFURANOSE
  • 1,2,3,5-TETRAACETYL-BETA-D-RIBOFURANOSE
  • Tetra-O-ribofuranose
  • B-D-Ribofuranose 1,2,3,5-Tetraacetate
  • Ribose tetracetate
  • Tetra-O-acetyl- Ribose
  • 1,2,3,5-Tetra-O-acetyl-β-D-ribofuranose ,98%
  • beta-D-Ribofuranose
  • 2,3,5-Tetra-O-acetyl-D-ribofuranose
  • 5-tetraacetate
  • beta-D-Ribofuranose 1
  • Β-D-RIBOFURANOSE TETRAACETATE
  • 1,2,3,5-Tetraacetate
  • <i>β</i>--D-Ribofuranose 1,2,3,5-Tetraacetate
  • Four acetyl RNA
  • Fouracetylribose
  • Regadenoson impurity G
  • Beta-D-Ribofuranose 1,2,3,5-tetraacetate(Ribavirin API Impurity H)
  • 1,2,3,5-Tetraacetoxy-β-D-Ribose
  • Tetra-O-acetyl-β-D-ribofuranose &gt
  • ?-D-Ribofuranose 1,2,3,5-tetraacetate