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| | (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol Basic information | | Uses |
| Product Name: | (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol | | Synonyms: | L-ALPHA,BETA-ISOPROPYLIDENEGLYCEROL;L-2,3-O-ISOPROPYLIDENE-SN-GLYCEROL;L-(-)-1,2-ISOPROPYLIDENEGLYCEROL;2,3-ISOPROPYLIDENE-SN-GLYCEROL;2,3-O-ISOPROPYLIDENE-L-GLYCEROL;(-)-2,3-O-ISOPROPYLIDENE-SN-GLYCEROL;R-GLYCEROL ACETONIDE;R-(-)-2,3-O-ISOPROPYLIDENEGLYCEROL | | CAS: | 14347-78-5 | | MF: | C6H12O3 | | MW: | 132.16 | | EINECS: | 604-360-5 | | Product Categories: | Chiral Reagents;Heterocycles;Inhibitors;Synthetic Organic Chemistry;Chiral Building Blocks;Dioxanes & Dioxolanes;Dioxolanes;Glycidyl Compounds, etc. (Chiral);pharmacetical | | Mol File: | 14347-78-5.mol |  |
| | (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol Chemical Properties |
| alpha | -13.7 º (neat) | | Boiling point | 72-73 °C/8 mmHg (lit.) | | density | 1.062 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.434 | | Fp | 176 °F | | storage temp. | 2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | Liquid | | pka | 14.20±0.10(Predicted) | | color | Clear colorless to light yellow | | Specific Gravity | 1.062 | | Optical Rotation | [α]20/D 13.7°, neat | | Water Solubility | miscible | | Merck | 14,5213 | | BRN | 80117 | | Stability: | Stable. Incompatible with strong oxidizing agents. | | InChI | 1S/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3/t5-/m1/s1 | | InChIKey | RNVYQYLELCKWAN-RXMQYKEDSA-N | | SMILES | CC1(C)OC[C@@H](CO)O1 | | CAS DataBase Reference | 14347-78-5(CAS DataBase Reference) | | NIST Chemistry Reference | D-Acetone glycerol(14347-78-5) |
| Safety Statements | 23-24/25 | | WGK Germany | 3 | | RTECS | JI0400000 | | F | 10 | | HS Code | 29329990 | | Storage Class | 10 - Combustible liquids |
| | (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol Usage And Synthesis |
| Uses | (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol is a MEK inhibitor with antitumor activity. | | Chemical Properties | colourless liquid | | Uses | A MEK inhibitor | | Uses | (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol may be used to prepare:
- (R)-2,2-Dimethyl-4-benzoxymethyl-1,3-dioxolane.
- ((S)-(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate)-1,3-dioxolane.
- (S)-Glyceraldehyde acetonide.
- Tetraoxaspiroundecanes, diglycerides, glyceryl phosphates, and spiropyrans.
| | Reactions | Versatile trichloromethyl carbinols can be prepared in one pot from primary alcohols by treatment with Dess–Martin periodinane (DMP) in CHCl3 followed by introduction of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). A modification of the method was used to convert chiral primary alcohol (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol to the corresponding trichloromethyl carbinol with complete stereochemical fidelity[1]. | | Synthesis | Using anhydrous zinc chloride as the catalyst, the condensation reaction of D-mannitol with acetone to synthesize the diisopropylidene condensate was carried out under the optimal reaction conditions, with a yield of up to 65%. Subsequently, (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol was obtained via chain cleavage by NaIO₄ oxidation and reduction with NaBH₄. | | References | [1] Gupta, M. K., Li, Z., & Snowden, T. S. (2012). One-Pot Synthesis of Trichloromethyl Carbinols from Primary Alcohols. Journal of Organic Chemistry, 77 10, 4854–4860. https://doi.org/10.1021/jo300725v
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| | (R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol Preparation Products And Raw materials |
| Raw materials | Ethanol-->Ethyl acetate-->Tetrahydrofuran-->Acetic acid-->Acetone-->Sodium borohydride-->p-Toluenesulfonic acid-->Tetrabutylammonium bromide-->Sodium periodate-->L(+)-Diethyl L-tartrate-->(2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester-->1,2:5,6-Bis-O-(1-methylethylidene)-D-mannitol | | Preparation Products | [(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methanamine-->(2,2-Dimethyl-[1,3]-dioxolan-4-yl)-methylamine-->2,2-Dimethyl-4(S)-4-iodomethyl-1,3-dioxalane |
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