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

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

Hebei Mojin 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

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-[5-13C]RIBOFURANOSIDE 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-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