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| | 1,3,5-Tri-O-benzoyl-D-ribofuranose Basic information |
| Product Name: | 1,3,5-Tri-O-benzoyl-D-ribofuranose | | Synonyms: | 1,3,5-TRI-O-BENZOYL-ALPHA-D-RIBOFURANOSE;1,3,5-TRI-O-BENZOYL-ALPHA-D-RIBOFURANOSIDE;1,3,5-Tri-O-benzoyl-D-ribofuranose;1,3,5-TRIBENZOATE-ALPHA-D-RIBOFURANOSE;[5-(benzoyloxy)-2-(benzoyloxymethyl)-4-hydroxyoxolan-3-yl] benzoate;ALPHA-D-RIBOFURANOSE 1,3,5-TRIBENZOATE;α-D-Ribofuranose, 1,3,5-tribenzoate;a-D-Ribofuranose, 1,3,5-tribenzoate | | CAS: | 22224-41-5 | | MF: | C26H22O8 | | MW: | 462.45 | | EINECS: | 606-957-6 | | Product Categories: | API intermediates;(intermediate of clofarabine);Sugars, Carbohydrates & Glucosides;22224-41-5 | | Mol File: | 22224-41-5.mol |  |
| | 1,3,5-Tri-O-benzoyl-D-ribofuranose Chemical Properties |
| Melting point | 125-129 °C(lit.) | | Boiling point | 629.6±55.0 °C(Predicted) | | density | 1.37±0.1 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | solubility | Chloroform (Slightly), Ethyl Acetate (Slightly) | | form | Powder | | pka | 12.35±0.70(Predicted) | | color | Pale brown | | Optical Rotation | [α]20/D +85.0°, c = 1 in chloroform | | Water Solubility | Insoluble in water, easily soluble in chloroform. | | λmax | 273nm(MeOH)(lit.) | | BRN | 98446 | | InChIKey | HUHVPBKTTFVAQF-QFBXJQHPSA-N | | SMILES | O(C(=O)C1=CC=CC=C1)C1O[C@H](COC(=O)C2=CC=CC=C2)[C@@H](OC(=O)C2=CC=CC=C2)[C@H]1O |&1:11,22,32,r| | | CAS DataBase Reference | 22224-41-5(CAS DataBase Reference) |
| Safety Statements | 22-24/25 | | WGK Germany | 3 | | HS Code | 29400090 |
| | 1,3,5-Tri-O-benzoyl-D-ribofuranose Usage And Synthesis |
| Chemical Properties | White to off-white powder | | Uses | It is employed as a starting material for nucleosides and is an intermediate fir cloforabine. | | Uses | Starting material for nucleosides. | | Synthesis | Synthesis of compound vi: Compound v (2.57 mmol) was dissolved in 26 mL of anhydrous dichloromethane, and the reaction lasted for 2.5 h under the condition of ice-water bath with slow passage of dry HCl gas. After completion of the reaction, the reaction solution was washed with 19.5 mL of ice water and the organic layer was separated. The organic layer was washed sequentially with saturated sodium bicarbonate solution until the aqueous layer was weakly basic, and then washed with ice water until the aqueous layer was neutral. The organic layer was dried with anhydrous sodium sulfate for more than 4 hours and subsequently concentrated under reduced pressure to give a light yellow syrupy product. The syrup was recrystallized using a solvent mixture of hexane and dichloromethane to give the white solid compound vi in 65.1% yield.1H NMR (CDCl3) δ ppm: 7.36-8.14 (m, 15H, OBz), 6.68 (d, J = 4.4 Hz, 1H, H-1), 5.59 (dd, 1H, H-3), 4.64-4.80 ( m, 4H, H-2, H-4 and H-5). Melting point: 139-140°C. | | References | [1] Patent: EP2177527, 2010, A1. Location in patent: Page/Page column 11
[2] Journal of Organic Chemistry, 1985, vol. 50, # 14, p. 2597 - 2598 |
| | 1,3,5-Tri-O-benzoyl-D-ribofuranose Preparation Products And Raw materials |
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