| Identification | More | [Name]
(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate | [CAS]
23735-43-5 | [Synonyms]
1,3-DIOXOLANE-4-METHANOL, 2,2-DIMETHYL-, 4-METHYLBENZENESULFONATE, (4S)-
2,2-DIMETHYL-4(S)-4-(P-TOLYLSULFONYL)METHYL-1,3-DIOXALANE
2,3-ISOPROPYLIDENE-SN-GLYCEROL 1-TOSYLATE
L-(+)-1,2-ISOPROPYLIDENEGLYCEROL 3-(P-TOLUENESULFONATE)
L-ALPHA,BETA-ISOPROPYLIDENEGLYCEROL-GAMMA-TOSYLATE
(S)-1,2-O-ISOPROPYLIDENEGLYCEROL-3-TOLUENESULFONATE
(S)-(+)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE
(S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL-4-METHYLBENZENESULFONATE
(S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL TOLUENE-4-SULFONATE
(S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL TOSYLATE
(S)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-YLMETHYL P-TOLUENESULFONATE
(S)-(+)-2,2-DIMETHYL-4-(HYDROXYMETHYL)-1,3-DIOXOLANE-P-TOLUENESULFONATE
(S)-2,2-DIMETHYL-4-(HYDROXYMETHYL)-1,3-DIOXOLANE-P-TOLUENESULFONATE
(S)-(+)-2,2-DIMETHYL-4-(HYDROXYMETHYL)-1,3-DIOXOLANE-P-TOLUENSULFONATE
(S)-3-TOSYLOXY-1,2-PROPANEDIOL ACETONIDE
(S)-O-ISOPROPYLIDENE GLYCEROL TOSYLATE
(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate
(S)-3-Toxyloxy-1,2-propanediol acetonide
(s)-2,2-dimethyl-1,3-dioxolane-4-methyl p-toluenesulfonate
(S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol 4-toluenesulfo | [Molecular Formula]
C13H18O5S | [MDL Number]
MFCD00063234 | [Molecular Weight]
286.34 | [MOL File]
23735-43-5.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
29-31 °C
| [alpha ]
4.2 º (c=10, abs.alcohol) | [Boiling point ]
398.71°C (rough estimate) | [density ]
1.208 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.506(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [form ]
powder to lump to clear liquid | [color ]
White or Colorless to Light yellow | [Optical Rotation]
[α]26/D +7.5°, c = 2% in DMF | [BRN ]
89799 | [InChI]
InChI=1/C13H18O5S/c1-10-4-6-12(7-5-10)19(14,15)17-9-11-8-16-13(2,3)18-11/h4-7,11H,8-9H2,1-3H3/t11-/s3 | [InChIKey]
SRKDUHUULIWXFT-LBPXTSNRNA-N | [SMILES]
C1(C=CC(C)=CC=1)S(=O)(=O)OC[C@@H]1COC(C)(C)O1 |&1:12,r| | [CAS DataBase Reference]
23735-43-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [F ]
10-21 | [HS Code ]
29329990 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [Uses]
(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate has been used as a reactant for the synthesis of 16-(3-trifluoromethyl)phenoxy PGF2α analog travoprost (T715600) which has potent topical ocular activity. (S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate has also been used for the preparation of p38 mitogen activated protein (MAP) kinase inhibitors. | [Synthesis]
The general procedure for the synthesis of (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate from p-toluenesulfonyl chloride and (R)-(-)-glycerol acetonide was carried out as follows: in accordance with the methodology used for the preparation of (R)-(-)-20a, (R)-(-)-2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolan-1,3-dioxolan (19b) ( 2.50 g) was converted to (S)-(+)-3-toluenesulfonyloxy-1,2-propanediol acetone compound 20b (5.23 g, 98% yield, 99.2% ee). [α]D20 +4.5 (c 1.0, EtOH) (literature value [α]D25 +4.7 (c 1.0, EtOH)).IR, NMR, and HRMS spectroscopic data were in complete agreement with the (R)-(-)-20a enantiomer. | [References]
[1] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 10, p. 1719 - 1723
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3198 - 3213
[3] Tetrahedron, 2013, vol. 69, # 5, p. 1634 - 1648
[4] Journal of the American Chemical Society, 1980, vol. 102, # 20, p. 6304 - 6311
[5] Journal of the Chemical Society, Chemical Communications, 1984, # 6, p. 349 - 350 |
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