Ethylene Oxide Type

The product retains, however, the configuration of D-galactose and is in fact methyl trimethyl-D-galactopyranoside (LII). The intermediate formation of a 1,3-anhydro ring is postulated. 

A curious observation made by Levene and Compton30, 31 is connected with the subject of this section. The saponification of 5-tosyl- 

3- isopropylidene-L-rhamnofuranose (n-rhamnose = 6-desoxy-L-manno-se) with sodium methoxide takes place in the cold and the product is methyl 2,3-isopropyIidene-6-desoxy-D-allofuranoside. Inversion occurs therefore not only on C5 but also on C4, and moreover Cl is also involved inasmuch as the displacing anion (OMe-) is ultimately located there in the product. The authors suggest that the reaction proceeds by virtue of the intermediate formation and scission of a 4,5-anhydro and a 1,5-anhydro compound, the foriner presumably having the configuration of D-gulose, the latter that of D-allose. 

Anhydro Sugars op the Hydropuranol Type 1. 3,6-Anhydro Hexoses 

This procedure provided the most important method for the synthesis of anhydro sugars of the hydrofuranol type. 3,6-Anhydro sugars have resulted from the saponification of hexoses esterified at C6 by the following cationogens Br- 3 36 14- 36 CH3 C H4 S020 37, 3S- 39 40 HO-SCVO-41 42 02N-0-.43 It is very probable that the phosphate ion is also cationogenic and that saponification of a hexose 6-phosphate 

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IV. The Scission of Anhydro Rings of the Ethylene Oxide Type. 47... 

The inference is that the hydrofuranol ring of XL can never be directly formed by the saponification of a 3-tosyl ester of D-glucose, but only indirectly by the intermediate formation and scission of an anhydro ring of the ethylene oxide type. The sequence of reactions involved in the conversion of methyl 3-tosyl-jS-D-gIueoside into methyl 3,6-anhydro-n-glucoside is shown by XXXVI to XL. 

L. F. Wiggins, Ethylene oxide-type anhydrosugars, Methods Carbohydr. Chem., 2 (1963) 188-191. 

To obtain the ethylene oxide type compound, /3-D-glucose pentaacetate was treated with an excess of phosphorus pentachloride to give 2-tri-chloroacetyl-3,4,6-triacetyl-/3-D-glucopyranosyl chloride.63,63a The tri-chloroacetyl group was removed by treatment with a dry ethereal solution of ammonia at 0°. From the product the anhydride may be obtained by... 

Radical transfer reactions involving poly ethers of the poly (ethylene oxide) type are well known (7). Heating polyethylene glycols of various molecular weights at 140 °C. with dicumyl peroxide for 2.5 hours has resulted in a gel fraction explained by transfer at the a-carbon followed by combination of the polymer radicals. Further, poly (ethylene oxide) dissolved in MMA and heated in the presence of benzoyl peroxide results in grafted copolymer. 

Possible Biocidal Effect. There has been some interest in whether the morpholine process has an effect comparable with that of an ethylene oxide-type fumigation process. Brief tests by a Coming Museum microbiologist in 1973 indicated that the process does have a significant value as a biocidal treatment, but these findings would require much more testing before a firm conclusion could be reached. 

CNC DISPERSION PE is a complex phosphate ester of nonionic surfactants of the ethylene oxide type. It is a 99% active substance and dissolves off-clear in water. It is the base or starting point of many novel products. 

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