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| | 1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose Basic information |
| Product Name: | 1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose | | Synonyms: | 1,3,4,6-TETRA-O-ACETYL-BETA-D-MANNOPYRANOSE;1,2,3,4-TETRA-O-ACETYL-BETA-D-MANNOPYRANOSE;1,3,4,6-Tetraacetate β-D-Mannopyranose;1,3,4,6-O-Tetraacetyl-β-D-Mannopyranose;[(2R,3R,4R,5S,6S)-3,4,6-triacetyloxy-5-hydroxyoxan-2-yl]methyl acetate;(2S,3S,4R,5R,6R)-6-(Acetoxymethyl)-3-hydroxytetrahydro-2H-pyran-2,4,5-triyl triacetate;1,3,4,6-Tetra-O-acetyl-β1,3,4,6-Tetra-O-acetyl-?D-mannopyranose | | CAS: | 18968-05-3 | | MF: | C14H20O10 | | MW: | 348.3 | | EINECS: | | | Product Categories: | Intermediates & Fine Chemicals;Labeling and Diagnostics Reagents;Pharmaceuticals;Carbohydrates & Derivatives;Biochemistry;O-Substituted Sugars;Sugars;chiral;Glycon Biochem | | Mol File: | 18968-05-3.mol |  |
| | 1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose Chemical Properties |
| Melting point | 160-161 °C(lit.) | | Boiling point | 425.5±45.0 °C(Predicted) | | density | 1.33±0.1 g/cm3(Predicted) | | refractive index | -22.5 ° (C=1.4, CHCl3) | | storage temp. | Sealed in dry,2-8°C | | solubility | very faint turbidity in Chloroform | | form | powder to crystal | | pka | 12.22±0.70(Predicted) | | color | White to Almost white | | Optical Rotation | [α]19/D 68°, c = 0.7 in pyridine | | BRN | 96634 | | InChI | InChI=1/C14H20O10/c1-6(15)20-5-10-12(21-7(2)16)13(22-8(3)17)11(19)14(24-10)23-9(4)18/h10-14,19H,5H2,1-4H3/t10-,11+,12-,13-,14-/s3 | | InChIKey | SHBHJRVMGYVXKK-XVIXHAIJSA-N | | SMILES | [C@@H]1(OC(=O)C)[C@@H](COC(=O)C)O[C@@H](OC(=O)C)[C@@H](O)[C@H]1OC(=O)C |&1:0,5,12,17,19,r| | | CAS DataBase Reference | 18968-05-3(CAS DataBase Reference) |
| Safety Statements | 22-24/25 | | WGK Germany | 3 | | HS Code | 29400090 | | Storage Class | 11 - Combustible Solids |
| | 1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose Usage And Synthesis |
| Uses | 1,3,4,6-Tetra-o-acetyl-beta-d-mannopyranose is an intermediate in the preparation of precursors of 2-[18F]fluoro-2-deoxy-D-glucose for diagnostic use in positron emission tomography. | | Synthesis | General procedure for the synthesis of (2S,3S,4R,5R,6R)-6-(acetyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2,4,5-triyl triacetate from 1,2-O-(1-ethoxyethylidene)-β-D-mannopyranose triacetate: to a solution of anhydrous acetone (27 mL) of the protoacid ester (4.4 g, 12 mmol), a slow addition of a 1 M aqueous hydrochloric acid (HCl) solution (2.7 mL), and the reaction was carried out under vigorous stirring (the water bath temperature was maintained at about 18 °C). The reaction mixture was continued to be stirred at room temperature for 5 min before being concentrated on a rotary evaporator, keeping the temperature below 20 °C. The concentrated solid was dissolved in chloroform (CHCl3, 25 mL) and washed with deionized water (2 x 10 mL). The organic phase was dried over anhydrous sodium sulfate (Na2SO4) and filtered, and the filtrate was concentrated on a rotary evaporator. The residue was ground with ether (Et2O) and recrystallized from ethanol (EtOH) to give the target product tetraacetylmannose (1.9 g, 45% yield) as a white solid. Thin layer chromatography (TLC) Rf value was 0.13 (unfolding agent: hexane/ethyl acetate = 1:1). The melting point is 134-136°C. High Resolution Mass Spectrometry (HRMS-ESI): m/z C14H20NaO10 ([M+Na]+) Calculated value 371.09542, measured value 371.09581 (error 0.39 mmu, 1.06 ppm). | | References | [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1848 - 1858
[2] Tetrahedron, 1992, vol. 48, # 47, p. 10249 - 10264
[3] Tetrahedron Letters, 2013, vol. 54, # 17, p. 2190 - 2193 |
| | 1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose Preparation Products And Raw materials |
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