67525-66-0

Basic information

• Product Name: beta-D-Ribofuranose 2,3,5-tribenzoate
• Synonyms: SS-D-RIBOFURANOSE, 2,3,5-TRIBENZOATE;2,3,5-TRI-O-BENZOYL-BETA-D-RIBOFURANOSE;2,3,5-TRI-O-BENZOYL-SS-D-RIBOFURANOSE;2,3,5-tribenzoate-β-D-Ribofuranose;2,3,5-tri-o-benzoyl-beta-d-ribose;[4-(Benzoyloxy)-2-(benzoyloxymethyl)-5-hydroxyoxolan-3-yl] benzoate;beta-d-ribofuranose 2,3,5-tribenzoate;β-D-Ribofuranose, 2,3,5-tribenzoate
• CAS NO: 67525-66-0
• Molecular Formula: C₂₆H₂₂O₈
• Molecular Weight: 462.45
• EINECS: 1312995-182-4
• Mol File: 67525-66-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 619.756 °C at 760 mmHg
• Flash Point: 209.15 °C
• Appearance: Yellow solid
• Density: 1.377 g/cm³
• Vapor Pressure: 3.21E-16mmHg at 25°C
• Refractive Index: 1.633
• Storage Temp.: 2-8°C
• CAS DataBase Reference: beta-D-Ribofuranose 2,3,5-tribenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: beta-D-Ribofuranose 2,3,5-tribenzoate(67525-66-0)
• EPA Substance Registry System: beta-D-Ribofuranose 2,3,5-tribenzoate(67525-66-0)

Safety Data

• Hazardous Substances Data: 67525-66-0(Hazardous Substances Data)

Usage

General Description

Beta-D-Ribofuranose 2,3,5-tribenzoate is a chemical compound derived from ribofuranose, a type of sugar. It is commonly used as a building block in the synthesis of nucleotide analogues and other bioactive molecules. beta-D-Ribofuranose 2,3,5-tribenzoate is a triester of ribose with three benzoyl groups attached at positions 2, 3, and 5. It is a white to off-white solid that is sparingly soluble in water but soluble in organic solvents. Beta-D-Ribofuranose 2,3,5-tribenzoate is used in research and pharmaceutical applications for its role in the modification of nucleosides and nucleotides, and it is also used as a chiral building block in organic synthesis.

InChI:InChI=1/C26H22O8/c27-23(17-10-4-1-5-11-17)31-16-20-21(33-24(28)18-12-6-2-7-13-18)22(26(30)32-20)34-25(29)19-14-8-3-9-15-19/h1-15,20-22,26,30H,16H2

Upstream product

• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 621-23-8 1,2,3-trimethoxybenzene 
• 98-88-4 benzoyl chloride 
• 7473-45-2 1-O-methyl-D-ribofuranose 
• 105330-91-4 2',3',5'-tri-O-benzoyl-6-methyl-5-azacytidine 
• 189129-04-2 C₃₀H₂₆N₄O₈ 
• 189129-08-6 C₃₀H₂₆N₄O₈ 
• 52783-53-6 methyl 2,3,3'-tri-O-benzoyl-β-D-apiofuranoside 
• 7408-41-5 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl azide 
• 36468-53-8 β-D-ribofuranose 

Downstream Products

• 13082-84-3 5,6-Dimethyl-1-β-D-ribofuranosyl-benzimidazol 
• 331942-39-3 N-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-3-nitrophthalimide 
• 14048-09-0 1-(2',3',5'-tri-O-benzoate-β-D-ribofuranosyl)-5-cyanouridine 
• 956485-73-7 C₃₉H₃₃NO₁₁ 
• 176696-99-4 1-((2R,3R,4R,5R)-3,4-Bis-benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-yl)-6-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 224175-68-2 C₃₈H₃₀ClNO₁₀ 
• 224175-70-6 ethyl 6-bromo-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-4-quinolone-3-carboxylate 
• 35068-46-3 1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-3-carbethoxy-7-methoxy-1,4-dihydrochinolin-4-on 
• 956485-77-1 C₃₉H₃₃NO₁₀ 
• 224175-69-3 C₃₈H₃₀BrNO₁₀ 
• 58-61-7 adenosine 
• 902458-65-5 C₃₁H₂₅N₅O₇ 
• 126193-21-3 C₃₁H₃₀N₄O₁₀ 
• 21823-89-2 2,3,5-tri-O-benzoyl-β-D-ribosyl isocyanate 

Relevant articles and documents

Novel phthalimide nucleosides for the specific recognition of a CG Watson-Crick base pair

In an effort to extend the triple helix recognition code we have synthesized various substituted phthalimide-derived nucleosides that can recognize a CG Watson-Crick base pair. NMR experiments performed on the free nucleosides in methylene chloride at lowered temperatures indicate the strength and extent of H-bonding to the cytosine amino group of a CG base pair which strongly depend on the substituent of the phthalimide nucleobase. Consistent with the formation of an additional hydrogen bond to N7 of guanine, ureido-substituted nucleoside analogs show a higher overall affinity as compared to the 3-aminophthalimide nucleoside.

6-Methyl-5-azacytidine - Synthesis, conformational properties and biological activity. A comparison of molecular conformation with 5- azacytidine

The title compound was prepared by the isocyanate procedure and the trimethylsilyl method. The measurement of 1H NMR spectrum of 6-methyl-5- azacytidine (1) revealed a preference of γ(t) (46%) rotamer around C(5')- C(4') bond, a predominance of N conformation of the ribose ring (K(eq) 0.33) and a preference of syn conformation around the C-N glycosyl bond. An analogous measurement of 5-azacytidine has shown a preference of γ+ (60%) rotamer around the C(5')-C(4') bond, a predominance of N conformation of the fibose ring (K(eq) 0.41) and a preference of anti conformation around the C- N glycosyl bond 6-Methyl-5-azacytidine (1) inhibits the growth of bacteria E coli to the extent of 85% at 4000 μM concentration and the growth of LoVo/L, a human colon carcinoma cell line, to the extent of 30% at 100 μM concentration but did not inhibit L1210 cells at ≤ 100 μM concentration 6- Methyl-5-azacytidine (1) exhibited no in vitro antiviral activity at ≤ 1 μM concentration.

Nucleoside Syntheses, XXII. Nucleoside Synthesis with Trimethylsilyl Triflate and Perchlorate as Catalysts

The novel Lewis acids (CH3)3SiOSO2CF3 (5), (CH3)3SiOSO2C4F9 (6), and (CH3)3SiClO4 (4) are highly selective and efficient Friedel-Crafts catalysts for nucleoside formation from silylated heterocycles and peracylated sugars as well as for rearrangements of persilylated protected nucleosides.With basic silylated heterocycles these new catalysts give much higher yields of the natural N-1-nucleosides than with SnCl4.