Erythritol Anhydride

Erythritol anhydride, bioxiran, butadiene dioxide, butanedione, 1,2,3,4-diepoxybutane. 

Erythritol anhydride (cis-2,3-dihydroxytetra-hydrofurane) 0° Highly reactive... 

SYNS BIOXIRANE 2,2 -BIOXIRANE BUTADIEN DIOXYD (GERMAN) BUTADIENE DIEPOXIDE 1,3-BUTADIENE DIEPOXIDE BUTADIENE DIOXIDE BUTANE DIEPOXIDE DEB DIEPOXYBUTANE 2,4-DIEPOXYBUTANE 1,2 3,4-DIEPOXYBUTANE DIOXYBUTADIENE ENT 26,592 ERYTHRITOL ANHYDRIDE RCRA WASTE NUMBER U085... 

Cyclic ethers are components of many natural products as well as synthetic compounds. A simple one is erythritol anhydride (63), which contains the epoxide unit and is used to prevent microbial spoilage. The important anticancer drug taxol (64) contains an oxetane unit. The tetrahydrofiiran unit is a component of the important carbohydrate ribose (65), which is the sugar portion of RNA (see Chapter 28). A tetrahydrofuran unit is found in isosorbide dinitrate (Isordil , 66), which is a vasodilator used in the prevention and treatment of angina. The tetrahydropyran unit is found in common sugars such as glucose (67) and in desosamine (68), which is the sugar component of many macrolide antibiotics. Both the tetrahydrofuran and tetrahydropyran rmits are found in the antibiotic Lasalocid (69). 

Ethylene oxide is an epoxy compound, and can also be named 1,2-epoxyethane. Diepoxy compounds are commercially important as components of epoxy adhesives. The simplest diepoxy compound is erythritol anhydride, or 1,2,3,4-diepoxybutane ... 

Erlenmeyer synthesis org chem Preparation of cyclic ethers by the condensation of an aldehyde with an a-acylamino acid in the presence of acetic anhydride and sodium acetate. 3r-l3n,mT-3r sin-th3-s3s erucic acid org chem C22H42O2 A monoethenoid acid that is the cis isomer of bras-sidic acid and makes up 40 to 50% of the total fatty acid in rapeseed, wallflower seed, and mustard seed crystallizes as needles from alcohol solution, insoluble in water, soluble in ethanol and methanol. o rus ik as ad erythrite See erythritol. er o.thrTt ... 

Hartman and R. Barker synthesized 1,4-anhydroerythritol (3) by the saponification of 1-O-p-tolylsulfonyl-D-erythritol (1). The reaction apparently proceeded by direct reaction of the 4-hydroxyl group with the 1-p-tolylsulfonoxy group, and not through the intermediate formation of the 1,2-anhydride, which would have afforded the epimer, namely, 1,4-anhydro-D-threitol (2). Similarly, 1-O-p-tolylsulfonyl-D-threitol gave 1,4-anhydro-D-threitol (2). 

Erythritol and L-threitol have also been dehydrated by means of 50% sulfuric acid at 120° to the corresponding 1,4-anhydrides.6 On heating erythritol in the presence of a small proportion of a xylene-sulfonic acid at 130-150° under vacuum, an 89% yield of 1,4-anhydro-DL-erythritol was obtained.7... 

Baddiley and coworkers8 speculated that the threitols would be more resistant to anhydride formation than erythritol, because their secondary hydroxyl groups are trnns-disposed. It is of interest that Klosterman and Smith,8 using somewhat more vigorous conditions, had found earlier, that, for anhydride formation, a lower temperature and shorter heating period could be used for erythritol than for threitol, thus lending support to this speculation. 

Erythritol is a white crystalline solid with a melting point of 121 C. (uncorrected). The anhydride, erythritan, prepared from erythritol by treatment with sulfuric acid is an almost colorless, mobile liquid which is water-soluble. 

Beck studied the acute toxicity, upon intraperitoneal injection, to mice of each compound. The anhydride was definitely less toxic. Erythritol in doses of 0.8 to 0.9 g. per 100 g. of mouse caused definite hypersensitivity, later convulsions, followed by death in two to three hours. Doses of 1.8 g. per 100 g. of mouse of erythritan produced convulsions followed by a lingering depression, ending usually in the death of the animal. 

Ring Scission of Cyclic Acetals. Part II, The Reactions of Di-O-methylenepenta-erythritol with Carboxylic Acids and Trifluoroacetic Anhydride, T. G. Bonner, E. J. Bourne, and N. M. Saville,/. Chem. Soc., 2917-2921 (1960). 

Figures. The C NMR spectrum of the oligomers of succinic anhydride and meso-erythritol (3 1 mole ratio) formed after 7 hours in r vxing diaxane. Structures in Scheme IV are similar to these.

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