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

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
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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)
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Safety

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

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
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
Sigma-Aldrich
Product number
PHR3472
Product name
Azacitidine Related Compound B
Purity
certified reference material, pharmaceutical secondary standard
Packaging
30MG
Price
$507
Updated
2024/03/01
Sigma-Aldrich
Product number
1045541
Product name
Azacitidine Related Compound B
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
15mg
Price
$1210
Updated
2024/03/01
TCI Chemical
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
TCI Chemical
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
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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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beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate Suppliers

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

Xinxiang Aurora Biotechnology Co.,Ltd.
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
Hebei Mujin Biotechnology Co.,Ltd
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
WUHAN FORTUNA CHEMICAL CO., LTD
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

6974-32-9, beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoateRelated Search:

1,2,3,5-TETRA-O-ACETYL-BETA-L-RIBOFURANOSE 1-O-Acetyl-3,5-bis-(4-chlorobenzoyl)-2-deoxy-D-ribose ALPHA-L-ERYTHRO-PENTOFURANOSYL CHLORIDE-2-DEOXY-BIS(4-METHYL BENZOATE) 1,3,5-Tri-O-benzoyl-D-ribofuranose 2,3-O-Isopropylidene-D-ribonic gamma-lactone 1,3,5-TRI-O-BENZOYL-ALPHA-L-RIBOFURANOSE 2,3-O-Isopropylidene-D-ribofuranoside 1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose 1-O-Methyl-2-deoxy-D-ribose (5-acetyloxy-3,4-dibenzoyloxy-oxolan-2-yl)methyl benzoate 1-ACETYL-2,3,5-TRI-O-BENZOYL-BETA-L-RIBOFURANOSE,1-O-ACETYL-2,3,5-TRI-O-BENZOYL-BETA-L-RIBOFURANOSE 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-D-RIBOFURANOSE beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate 1-O-Acetyl-2,3,5-tri-O-(4-chlorobenzoyl)-beta-D-ribofuranose 1,2,3,5-Tetra-O-benzoyl-2C-methyl-D-ribofuranose 1-O-ACETYL 2,3,5-TRI-O-BENZOYL-BETA-D-[1-13C]RIBOFURANOSIDE 1-O-ACETYL 2,3,5-TRI-O-BENZOYL-BETA-D-[UL-13C5]RIBOFURANOSIDE 1-O-ACETYL 2,3,5-TRI-O-BENZOYL-BETA-D-[5-13C]RIBOFURANOSIDE

  • 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
  • beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate,98%
  • ACETYLTRIBENZOYLRIBOSE
  • 1-ACETYL-2,3,5-TRIBENZOY-B-D-RIBOFURANOSE
  • 1-ACETYL-2,3,5-TRIBENZOYL-B-D-RIBOFURANOSE
  • 1-ACETYL-2,3,5-TRIBENZOYL-BETA-D-RIBOFURANOSE
  • 1-ACETYL-2,3,5-TRIBENZOYL-BETA-D-RIBOFURANOSIDE
  • 2,3,5-TRI-O-BENZOYL-1-O-ACETYL-BETA-D-RIBOFURANOSE
  • 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-BETA-RIBOFURANOSE
  • 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-D-RIBOFURANOSIDE
  • 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSE
  • 1-O-ACETYL-2,3,5-TRIBENZOYL-BETA-D-RIBOFURANOSIDE
  • 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-B-D-RIBOFURANOSE
  • 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-BETA-ARABINOFURANOSIDE
  • 1-0-Acetyl-2,3,5-Tri-0-Benzoyl-Beta-D-Ribofuranose
  • 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose ,98%
  • 1-Acetyl-2
  • 5-tribenzoyl-beta-D-ribofuranose
  • 1-acetate 2,3,5-tribenzoate-β-D-Ribofuranose
  • 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 1-O-acetyl-2',3',5'-tri-O-benzoyl-β-D-ribofuranose
  • 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribose
  • 2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl Acetate
  • ABR
  • NSC 23349
  • β-D-Ribofuranose 1-Αcetate 2,3,5-Tribenzoate
  • 1-O-Acetyl-2,3,5-tri-O-benzoyl-β,DL-ribofuranose
  • Azacitidine USP Related Compound B
  • 1-acetate 2,3,5-tribenzoate-beta-D-Ribofuranose
  • Azacetidine Related Compound B
  • 1-Ac- 2,3,5-Bz- beta-D-Ribofuranose
  • 1-O-Acetyl-2,3,5-Tri-O-benzoyl-beta-D-Ribofuranosine
  • β-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate
  • 1-O-ACETYL-2,3,5-TRIBENZAMIDE-D-RIBOSE
  • 2,3,5-TRI-O-BENZOYL-1-O-ACETYL-β-D-RIBOFURANSE
  • 1-O-Acetyl-2,3,5-O-tribenzoyl-β-D-ribofuranose
  • beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate, 99+%
  • 1-Acetyl-2,3,5-tribenzoy-beta-D-ribofuranose
  • 1-O-Acetyl-2,3,5-tri-O-benzoyl-a,b-D-ribofuranose
  • 1-o-acetyl-2,3,5-tri-o-benzoyl-á-d-ribofuranose
  • B-D-RIBOFURANOSE
  • 1-O-Acetyl Tribenzoyl-B-D-Ribofuranose
  • RibofuranoseAcetateTribenzoate
  • SS-D-RIBOFURANOSE 1-ACETATE 2,3,5-TRIBENZOATE
  • 1-O-Ac-2,3,5-tri-O-bz-β-D-ribofuranose
  • á-d-ribofuranose 1-acetate 2,3,5-tribenzoate
  • 1-O-ACETYL-2,3,5-TRI-O-BENZOYL-SS-D-RIBOFURANOSE
  • 1-Acetyl-2,3,5-tri-O-benzoyl-B-D-ribofuranose
  • 1-ACETYL-2, 3, 5-TRI-O-BENZOYL-β-D-RIBOFURANOSE
  • (2S,3R,4R,5R)-2-acetoxy-5-(benzoyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate
  • 1-O-Acetyl-2,3,5-Tri-O-Benzoly-Beta-D-Ribofuranse Min98% C1
  • 1-O-acetyl 2,3,5-tri-O-benzoyl-β-d-[1-13C]ribofuranoside