6-Hydroxymethyl-2,2-dimethyl-dihydro-furo(3,4-d)(1,3)dioxol-4-one
(3aR,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one · 2,3-ISOPROPYLIDENE-D-RIBONOLACTONE · 2,3-ISOPROPYLIDENE-D-RIBONO-1,4-LACTONE · 2,3-O-Isopropylidene-D-ribonic acid-1,4-lactone · ISOPROPYLIDENE-D-RIBONOLACTONE · 2,3-O-Isopropylidine-D-ribonolactone · 2,3-O-Isopropylidene-D-ribonolactone · 2,3-O-lsopropylidene-D-ribonolactone
Identifikatoren & physikalische Daten
| CAS No. | 30725-00-9 |
|---|---|
| Summenformel | C8H12O5 |
| Durchschnittliche Molmasse | 188,18 g/mol |
| Monoisotopische Masse | 188,06847348 g/mol |
| SMILES | CC1(C)OC2C(=O)OC(CO)C2O1 |
| InChIKey | NHHKFJCWLPPNCN-UHFFFAOYSA-N |
| PubChem CID | 500172 |
| EC No. | 608-517-9 |
Chemische & physikalische Eigenschaften
| XLogP | -0,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 65 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 237 |
| Schmelzpunkt | 135-139 °C |
| Siedepunkt | 243.17°C (rough estimate) |
| Dichte | 1.2069 (rough estimate) |
| Brechungsindex | 1.4348 (estimate) |
| Lagerbedingungen | Keep in dark place,Sealed in dry,Room Temperature |
| Löslichkeit | Soluble in methanol at 50mg/ml, acetone, dichloromethane, ethyl Acetate. |
| pKa (Säurekonstante) | 13.68±0.10(Predicted) |
| Aggregatzustand | Powder |
| Farbe | White to Off-white |
| BRN | 10090 |
| InChI | InChI=1/C8H12O5/c1-8(2)12-5-4(3-9)11-7(10)6(5)13-8/h4-6,9H,3H2,1-2H3/t4-,5-,6-/s3 |
| InChIKey | NHHKFJCWLPPNCN-WKRIEWPCNA-N |
| SMILES | [C@H]12OC(C)(C)O[C@H]1C(O[C@@H]2CO)=O |&1:0,6,9,r| |
| CAS Datenbank | 30725-00-9(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | Not Classified |
|---|---|
| Hazard Classes and Categories | Not Classified |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29322090 |
| Sicherheitshinweise (S) | 22-24/25 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
2,3-Isopropylidene-D-ribonolactone is a building block. It has been used in the stereocontrolled synthesis of the carbohydrates 6-epi-trehazolin and 6-epi-trehalamine.
Verwenden
2,3-O-Isopropylidene-D-ribonic acid-1,4-lactone is used for the synthesis of C-nucleosides, prostanoids and GABA analogs via homochiral 2-piperidones. It is the starting material for the preparation of biochemical compounds including C-nucleosides, such as neplanocin A, and GABA analogs, via homochiral 2-piperidones.