| Identification | More | [Name]
beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate | [CAS]
6974-32-9 | [Synonyms]
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
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-O-ACETYL-2,3,5-TRI-O-BENZOYL-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-BENZYL-BETA-D-RIBOFURANOSE
2,3,5-TRI-O-BENZOYL-1-O-ACETYL-BETA-D-RIBOFURANOSE
ACETYLTRIBENZOYLRIBOSE
B-D-RIBOFURANOSE-1-ACETATE-2,3,5-TRIBENZOATE
BETA-D-RIBOFURANOSE 1-ACETATE 2,3,5-TRIBENZOATE
1-O-Acetyl-2,3,5-Tri-O-benzoyl-beta-D-Ribofuranosine
β-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate
B-D-RIBOFURANOSE
1-O-Acetyl Tribenzoyl-B-D-Ribofuranose
RibofuranoseAcetateTribenzoate | [EINECS(EC#)]
230-220-4 | [Molecular Formula]
C28H24O9 | [MDL Number]
MFCD00005357 | [Molecular Weight]
504.48 | [MOL File]
6974-32-9.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [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. ]
2-8°C
| [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 | [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]
6974-32-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/38:Irritating to eyes and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [TSCA ]
Yes | [HS Code ]
29400000 |
| Hazard Information | Back Directory | [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.] |
| Spectrum Detail | Back Directory | [Spectrum Detail]
beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate(6974-32-9)MS
beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate(6974-32-9)1HNMR
beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate(6974-32-9)13CNMR
beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate(6974-32-9)IR1
beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate(6974-32-9)IR2
beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate(6974-32-9)Raman
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