Eastman introduces 3,4-Epoxy 1-butene derivatives

Expanding offering to pharmaceutical and fine chemical customers

The Fine Chemicals business of Eastman Chemical Co. (Kingsport, TN) has introduced a family of new chiral derivatives of epoxybutene targeted to pharmaceutical developers. The compounds include such novel alpha-amino acids as cyclopropylglycine and derivatives; beta-amino acids including cyclopropyl-beta-alanine derivatives; and various 3, 4-dihydroxy- tetrahydrofuran species.

Chiral 3,4-Epoxy-1-butene (EPB) is a small molecule packed with potential for both manufacturing and discovery scientists. No two carbons are chemically or stereochemically equivalent. Couple that to chirality at C-3 and it's possible to create a host of interesting chiral materials based on epoxide ring-opening or addition/oxidation of the double bond.

Although it has been known for at least a century, EPB was never seriously considered as a manufacturing intermediate because of its high cost. Eastman's development of a continuous air oxidation process for butadiene has made EPB economical.

The new additions round out Eastman's chiral EpB derivative portfolio, which includes both enantiomers of EpB oxirane itself (3,4-epoxy-1-butene); EpB diol (3,4-dihydroxy-1-butene) and derivatives; and 2-amino-3-butene-1-ol and derivatives.

While the latest chiral EpB derivatives provide specific answer pharmaceutical industry needs, Eastman Fine Chemicals pharmaceutical unit manager W. Andrew Clark says the company can apply the underlying technologies to a broader base of chiral compounds.

Eastman plans to divest both chiral and nonchiral EpB derivatives under a previously announced plan to sell off portions of its Fine Chemicals business.

Edited by Angelo DePalma
Managing Editor, Drug Discovery Online and Pharmaceutical Online
Email: adepalma@vertical.net