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| | 2,3-O-ISOPROPYLIDENE-1-O-METHYL-D-RIBOSIC ACID Basic information |
| Product Name: | 2,3-O-ISOPROPYLIDENE-1-O-METHYL-D-RIBOSIC ACID | | Synonyms: | 2,3-O-ISOPROPYLIDENE-1-O-METHYL-D-RIBOSIC ACID;Methyl 2,3-O-isopropylidene-beta-D-ribofuranosiduronic acid;methyl 2,3-o-isopropylidene-á-d-ribofuranosiduronic acid;2,3Isopropylidene-1methyl-D-ribosic acid, 97%;(3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid;(3AS,6R,6AR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid;(3AS,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid;1-Methoxy-2,3-O-isopropylidene-β-D-ribofuranosyl-5-carboxylic acid | | CAS: | 54622-95-6 | | MF: | C9H14O6 | | MW: | 218.2 | | EINECS: | | | Product Categories: | | | Mol File: | 54622-95-6.mol |  |
| | 2,3-O-ISOPROPYLIDENE-1-O-METHYL-D-RIBOSIC ACID Chemical Properties |
| Melting point | 129-130°C | | Boiling point | 341.6±42.0 °C(Predicted) | | density | 1.34±0.1 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | solubility | Soluble in methanol. | | pka | 2.67±0.60(Predicted) | | Appearance | White to light yellow Solid | | Optical Rotation | -67.369° (C=0.01 g/ml, CHCL3) | | InChI | InChI=1/C9H14O6/c1-9(2)14-4-5(7(10)11)13-8(12-3)6(4)15-9/h4-6,8H,1-3H3,(H,10,11)/t4-,5,6-,8/s3 | | InChIKey | BTFKDZSYIKUCGF-DSRBPVEZNA-N | | SMILES | [C@]12([H])OC(C)(C)O[C@@]1([H])C(OC2C(=O)O)OC |&1:0,7,r| |
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ALFA
| English |
| | 2,3-O-ISOPROPYLIDENE-1-O-METHYL-D-RIBOSIC ACID Usage And Synthesis |
| Synthesis | General procedure for the synthesis of 2,3-o isopropylidene-1-o-methyl-d-ribonucleic acid from (3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxydan-4-yl)methanol: At 0 °C, KBr (1.70 g, 14.7 mmol) and TEMPO (0.383 g 2.45 mmol) were added to a solution of (3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (10.0 g, 49.0 mmol) in EtOAc (100 mL), followed by the titrative addition of NaOCl (12%, 39.5 mL. 63.7 mmol). The reaction solution was adjusted to pH 2 with 35% HCl, followed by the addition of 25% aqueous NaCl (5.76 g, 63.7 mmol) over 30 min, keeping stirring at room temperature. The reaction lasted for 7 h and was completed. The pH was adjusted to 2-3 and the product was extracted with EtOAc. The organic phases were combined, washed with brine, dried over MgSO4, filtered and the solvent was concentrated under reduced pressure to give the crude product. The crude product was purified by recrystallization from n-hexane in hot CH2Cl2 to give a white solid; Yield: 10.68 g (quantitative); Melting point: 128.5-129.5 °C (literature value 27b: 129-131 °C); [α]D20.5 -67.29 (c 2.47, CHCl3).1H NMR (CDCl3, 400 MHz): δ= 10.69 (s, 1H), 5.20 (d, J = 6.3Hz, 1H), 5.09 (s, 1H), 4.69 (s, 1H), 4.59 (d, J = 6.0Hz, 1H), 3.45 (s, 3H), 1.50 (s, 3H), 1.34 (s, 3H). | | References | [1] Chemistry - A European Journal, 2006, vol. 12, # 20, p. 5246 - 5252
[2] Synthesis (Germany), 2017, vol. 49, # 18, p. 4299 - 4302
[3] Tetrahedron, 1991, vol. 47, # 4-5, p. 715 - 724
[4] Journal of the American Chemical Society, 1958, vol. 80, p. 5168,5173
[5] Journal of Medicinal Chemistry, 2004, vol. 47, # 16, p. 4041 - 4053 |
| | 2,3-O-ISOPROPYLIDENE-1-O-METHYL-D-RIBOSIC ACID Preparation Products And Raw materials |
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