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| | 1,2,3,4,6-Penta-O-acetyl-alpha-D-mannopyranose Basic information |
| Product Name: | 1,2,3,4,6-Penta-O-acetyl-alpha-D-mannopyranose | | Synonyms: | A-D-mannosepentaacetate;ACETIC ACID (2R,3R,4S,5S,6R)-3,4,5,6-TETRAACETOXY-TETRAHYDRO-PYRAN-2-YLMETHYL ESTER;1-O,2-O,3-O,4-O,6-O-Pentaacetyl-α-D-mannopyranose;Penta-O-acetyl-alpha-D-mannopyranose;1,2,3,4,6-O-Pentaacetyl-alpha-mannose;1,2,3,4,6-Penta-O-acetyl-alpha-D-mannose;2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranosyl acetate;alpha-D-Mannopyranose,1,2,3,4,6-pentaacetate | | CAS: | 4163-65-9 | | MF: | C16H22O11 | | MW: | 390.34 | | EINECS: | 609-945-9 | | Product Categories: | Carbohydrates & Derivatives;13C & 2H Sugars;Glycon Biochem | | Mol File: | 4163-65-9.mol |  |
| | 1,2,3,4,6-Penta-O-acetyl-alpha-D-mannopyranose Chemical Properties |
| Melting point | 64-75°C | | Boiling point | 135 °C(Press: 0.0001 Torr) | | density | 1.30 | | storage temp. | Sealed in dry,Store in freezer, under -20°C | | solubility | Soluble in chloroform | | form | Powder | | color | White to Off-white | | InChI | InChI=1/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12-,13-,14+,15+,16+/s3 | | InChIKey | LPTITAGPBXDDGR-OWYFMNJBSA-N | | SMILES | [C@@H]1(OC(=O)C)[C@H](OC(=O)C)[C@H](O[C@H](COC(=O)C)[C@H]1OC(=O)C)OC(=O)C |&1:0,5,10,12,18,r| | | CAS DataBase Reference | 4163-65-9(CAS DataBase Reference) |
| WGK Germany | 3 | | Storage Class | 11 - Combustible Solids |
| | 1,2,3,4,6-Penta-O-acetyl-alpha-D-mannopyranose Usage And Synthesis |
| Uses | 1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-MANNOPYRANOSE was used for glycosylation in a study that assessed novel synthetic inhibitors of selectin-mediated cell adhesion. 1 It has also been used in a study to investigate stereospecific entry to spiroketal glycosides using alkylidenecarbene CH insertion. | | Uses | 1,2,3,4,6-Penta-O-acetyl-α-D-mannopyranose (cas# 4163-65-9) is a compound useful in organic synthesis. | | Synthesis | D-Anhydrous glucose (3.00 g, 16.6 mmol) was dissolved in anhydrous pyridine (33 mL) and acetic anhydride (31.5 mL, 333 mmol) was added slowly and dropwise at 0 °C and under nitrogen protection. The reaction mixture was stirred at 0 °C for 1 h. After that, a catalytic amount of DMAP (200 mg, 1.67 mmol) was added. Subsequently, the reaction mixture was gradually warmed up to room temperature, during which a slight exothermic phenomenon was observed. After 6 hours of reaction, the clarified yellow reaction solution was slowly poured into rapidly stirred ice water (125 mL) and a viscous solid was precipitated. After extraction by ethyl acetate (345 mL), the solvent was evaporated and co-evaporated with anhydrous toluene (320 mL) to give the final fully acetylated glucose as a yellow solid (5.84 g, 90% yield). | | References | [1] Angewandte Chemie, International Edition, 2009, vol. 48, p. 2723 - 2726
[2] Angewandte Chemie, 2009, vol. 121, p. 2761 - 2764
[3] Tetrahedron, 2013, vol. 69, # 41, p. 8731 - 8737
[4] Green Chemistry, 2011, vol. 13, # 1, p. 59 - 63
[5] Journal of the Chinese Chemical Society, 2009, vol. 56, # 2, p. 398 - 403 |
| | 1,2,3,4,6-Penta-O-acetyl-alpha-D-mannopyranose Preparation Products And Raw materials |
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