4- Deoxy-hexoses

In extending this direct method of synthesis, we next investigated the possibility of preparing similarly constituted halides from 2-deoxy-D-arabino-hexose (2-deoxy-D-glucose) (21). The hexose was subjected to a partial anomerization procedure described by Bergmann and co-workers (1). The solid material obtained by this procedure is a mixture of the anomeric forms of 2-deoxy-D-arabino-hexose low temperature p-nitro-benzoylation of the latter in pyridine resulted in a mixture of crystalline, anomeric tetrakis-p-nitrobenzoates in a ratio of approximately 1 1. They were readily separable by fractional recrystallization, and treatment of either with an excess of hydrogen bromide in dichloromethane, or with... 

Y. Margaret, H. Wong, and G. R. Gray, 2-deoxy-D-arafono-hexose, 2-deoxy-D-/yxo-hexose, and their (2R)-2-deuterio analogs, Carbohydr. Res., 80 (1980) 87-98. 

D. Horton, T.-M. Cheung, and W. Weckerle, 2,6-Dideoxy-D-/yxo-hexose (2-deoxy-L-fucose), Method. Carbohydr. Chem., 8 (1980) 201-205. 

DACHIY. 2-Deoxy-/ -D-lyxo-hexose 2-deoxy-/ -D-galactose (CgH Os). Puliti R, Mattia CA, Barone G (1984) Carbohydr Res 135 47... 

Later workers have also made use of the carbonate grouping as a protecting group, for example, in the synthesis of 3-0-methyl-D-galactose, 2-deoxy-3-0-methyl-D-a 2/io-hexose, 2-deoxy-D-er2/[Pg.93]

SYNS 2-DEOXY-d-ARABINO-HEXOSE 2-DEOXY-3-ARABINO-HEXOSE d-2-DEOXYGLUCOSE 2-DEOXY-d-GLUCOSE 2-DEOXY-d-GLUCOSE (FRENCH) 2-DG NSC-15193... 

Deoxy-D-arabtno-hexose ( 2-deoxy-D-glucose ) is not a substrate for the growth, respiration, or fermentation of yeasts. However, it is metabolized, although the extent to which the hexose ring is cleaved is small. The compound is phosphorylated by hexokinase, with ATP as the donor.3660 2-Deoxy-D-arabtno-hexose is employed as an ana-... 

All of the above compounds have cis double bonds it is not known whether trans forms, which must be acyclic, exist. The low yields of enol ethers obtained by the action of alkali on some 2-0-methylaldoses may be due to the formation of 3,6-anhydroaldoses. For example, 3,6-anhydro-2-deoxy-D-ami no-hexose is formed reversibly from 2-deoxy-o-arabino-hexose ( 2-deoxy-n-glucose ) by the action of alkali. Another possibility is the formation of 5-(l,2-dihydroxyethyl)-3-methoxyfuran by analogy with the reaction of (53) to give (54) (see Section VII, la p. 202). 

Anion-exchange chromatography has been used to separate sugar-borate complexes of D-mannose, L-fucose, D-galactose, D-glucose, D-xylose, L-arabinose, 2-amino-2-deoxy-D-mannose, 2-amino-2-deoxy-D-galactose, l-dcoxy-Ji-arabino-hexose, 2-deoxy-D-/yx u-hexose, and lactose. This technique was used to study the composition of the carbohydrate moieties of ovomucoid, lichenin, and Collocalia mucoid. 

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