(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate Chemical Properties

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.)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,2-8°C

form 

powder to lump to clear liquid

color 

White or Colorless to Light yellow

optical activity

[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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

F 

10-21

HS Code 

29329990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate Usage And Synthesis

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

(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate(23735-43-5)Related Product Information

• ETHANE
• Dimethyl sulfoxide
• Methanol
• Xylene
• Dimethyl sulfate
• Dimethyl phthalate
• Sulfanilic acid
• N,N-Dimethylformamide
• Calcium dobesilate
• Amlodipine Besylate
• p-Toluenesulfonic acid
• Dimethyl ether
• Dodecylbenzenesulphonic acid
• Benzenesulfonic acid
• Linear alkyl benzenesulphonate
• Dimethyl carbonate
• Dimethyl fumarate
• Dacthal