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beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate

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beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate Basic information

Product Name:
beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate
Synonyms:
  • 1-O-Acetyl-2,3,5-tri-O-benzoyl-a,-D-ribofuranose
  • B-D-RIBOFURANOSE-1-ACETATE-2,3,5-TRIBENZOATE
  • BETA-D-RIBOFURANOSE 1-ACETATE 2,3,5-TRIBENZOATE
  • 1-O-Acetyl-2-O,3-O,5-O-tribenzoyl-β-D-ribofuranose
  • 2-O,3-O,5-O-Tribenzoyl-1-O-acetyl-β-D-ribofuranose
  • 2-O,3-O,5-O-Tribenzoyl-β-D-ribofuranose 1-acetate
  • (3R,4R,5R)-2-Acetoxy-3,4-bis(benzoyloxy)-5-(benzoyloxymethyl)tetrahydrofuran
  • 1-0-Acetyl-2,3,5-Tri-0-Benzoyl--D-Ribofuranose
CAS:
6974-32-9
MF:
C28H24O9
MW:
504.48
EINECS:
230-220-4
Product Categories:
  • 50kg in stock
  • Carbohydrates
  • Pharmaceutical Intermediates
  • chiral
  • (intermediate of clofarabine)
  • Nucleic acids
  • Sugars, Carbohydrates & Glucosides
  • Biochemistry
  • Nucleosides, Nucleotides & Related Reagents
  • O-Substituted Sugars
  • Ribose
  • Riboses and 2'-Deoxyriboses
  • Sugars
  • Inhibitors
  • Carbohydrates & Derivatives
  • 6974-32-9
Mol File:
6974-32-9.mol
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beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate Chemical Properties

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)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/38
Safety Statements 
22-24/25-37/39-26
WGK Germany 
3
TSCA 
Yes
HS Code 
29400090

MSDS

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beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate Usage And Synthesis

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.]

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