beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate
- Product Name
- beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate
- CAS No.
- 6974-32-9
- Chemical Name
- beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate
- Synonyms
- 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose;ABR;NSC 23349;1-Acetyl-2;1-O-AcetyL;B-D-RIBOFURANOSE;-β-D-ribofuranose;-2,3,5-tri-O-benzoyL;ACETYLTRIBENZOYLRIBOSE;Azacetidine Related Compound B
- CBNumber
- CB3292813
- Molecular Formula
- C28H24O9
- Formula Weight
- 504.48
- MOL File
- 6974-32-9.mol
beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate Property
- Melting point:
- 128-130 °C
- alpha
- 24.4 º (c=1, pyridine)
- Boiling point:
- 621.0±55.0 °C(Predicted)
- Density
- 1.35±0.1 g/cm3(Predicted)
- refractive index
- 24 ° (C=1, Pyridine)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Sonicated),
- form
- Liquid
- color
- Clear slightly yellow or greenish to brown
- optical activity
- [α]20/D +24.3°, c = 1 in pyridine
- BRN
- 100243
- InChI
- InChI=1/C28H24O9/c1-17(29)34-28-24(36-26(31)19-13-7-4-8-14-19)23(35-25(30)18-11-5-3-6-12-18)22(37-28)20-15-9-10-16-21(20)27(32)33-2/h3-16,22-24,28H,1-2H3/t22-,23-,24-,28-/s3
- InChIKey
- GCZABPLTDYVJMP-CBUXHAPBSA-N
- SMILES
- C(OC)(=O)C1=CC=CC=C1[C@@H]1[C@@H](OC(=O)C2=CC=CC=C2)[C@@H](OC(=O)C2=CC=CC=C2)[C@H](OC(C)=O)O1 |&1:10,11,21,31,r|
- CAS DataBase Reference
- 6974-32-9(CAS DataBase Reference)
- EPA Substance Registry System
- .beta.-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate (6974-32-9)
Safety
- Hazard Codes
- Xi
- Risk Statements
- 36/38
- Safety Statements
- 22-24/25-37/39-26
- WGK Germany
- 3
- TSCA
- Yes
- 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.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 159018
- Product name
- β-D-Ribofuranose 1-acetate 2,3,5-tribenzoate
- Purity
- 98%
- Packaging
- 1g
- Price
- $32.1
- Updated
- 2024/03/01
- Product number
- PHR3472
- Product name
- Azacitidine Related Compound B
- Purity
- certified reference material, pharmaceutical secondary standard
- Packaging
- 30MG
- Price
- $507
- Updated
- 2024/03/01
- Product number
- 1045541
- Product name
- Azacitidine Related Compound B
- Purity
- United States Pharmacopeia (USP) Reference Standard
- Packaging
- 15mg
- Price
- $1210
- Updated
- 2024/03/01
- Product number
- R0067
- Product name
- β-D-Ribofuranose 1-Acetate 2,3,5-Tribenzoate
- Purity
- >98.0%(HPLC)
- Packaging
- 5g
- Price
- $76
- Updated
- 2024/03/01
- Product number
- R0067
- Product name
- β-D-Ribofuranose 1-Acetate 2,3,5-Tribenzoate
- Purity
- >98.0%(HPLC)
- Packaging
- 25g
- Price
- $191
- Updated
- 2024/03/01
beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate Chemical Properties,Usage,Production
Description
β-D-Ribofuranose 1-Acetate 2,3,5-Tribenzoate is an optically active ribose derivative. It is white to orange to green powder to crystals, slightly soluble in methanol, and can be used as a starting material for nucleoside synthesis. The substance is also used as an intermediate for Clofarabine, which belongs to a class of drugs called purine nucleoside antimetabolites and is used to treat acute lymphoblastic leukemia (ALL) in children and young adults aged 1 to 21 years.
Chemical Properties
white to light yellow crystal powde
Uses
An inhibitor of neutrophil-keyhole limpet hemocyanin adhesion
Application
Beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate, also known as 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose, is a ribose-derived compound used in nucleoside synthesis.
Definition
The commonly used 1-O-acetyl-2,3,5- tri-O-benzoyl-β-D-ribofuranose (beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate) can be employed in the glycosylation of 7-deazapurines when 7-halogenated nucleobases are used. Using common ribosugars such as 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose resulted in the formation of orthoamides when the pyrrole ring was not functionalized. The glycosylation yield and glycosylation position of 7-deazapurines with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose depends strongly on 7-substituents (H vs halogen) and amino protecting groups. It could be used to synthesize 5-Bromo-4-chloro-2-[(N2-isobutyryl){2,3,5-tri-O-benzoyl-β-Dribofuranosyl}]amino-7H-pyrrolo[2,3-d]pyrimidine.
Synthesis
Rac-(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-hydroxytetrahydrofuran-3,4-diyl dibenzoate was dissolved in dry pyridine, and the solution was slowly added dropwise with acetic anhydride in an ice water bath, then stirred for 30 minutes. Then, the ice water bath was removed, and the solution was stirred at room temperature for 7 hours and then heated to 40°C. This temperature was kept for an hour. The solution was added with broken ice and then stirred until the broken ice melted. The reaction solution was poured into ice water and extracted with chloroform. The organic layer was washed sequentially with ice water, pre-cooled sulfuric acid, and saturated sodium bicarbonate until the water layer showed weak alkaline, then washed with ice water until the water layer showed neutral, dried over anhydrous sodium sulfate for more than 4 hours, and then drawn off under reduced pressure, to obtain the light yellow syrup-like beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate (92.1%).
Purification Methods
Recrystallise it from EtOH or isoPrOH. [Helv Chim Acta 42 1171 1959, NMR: J Org Chem 33 1799 1968, IR: Chem Pharm Bull Jpn 11 188 1963, Beilstein 17/6 V 213.]
beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate manufacturers
- Product
- beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate 6974-32-9
- Price
- US $0.00-0.00/Kg
- Min. Order
- 1Kg
- Purity
- 98%
- Supply Ability
- 20Ton
- Release date
- 2024-11-01
- Product
- beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate 6974-32-9
- Price
- US $0.00-0.00/Kg/Drum
- Min. Order
- 1KG
- Purity
- 98%min HPLC
- Supply Ability
- 10 Tons
- Release date
- 2021-06-04
- Product
- beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate 6974-32-9
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99.3%
- Supply Ability
- 50000KG/month
- Release date
- 2024-10-23