2-Deoxy-3-0-methyl-D-glucose

Only unusual sugars are listed in Table 13, of which 2-deoxy-D-glucose (835), 2-deoxy-3-0-methyl-D-glucose (836) and 3,6-anhydro-2-... 

Deoxy-3-0-methyl-D-glucose Pteris inaequalis var. aequata Tagawa = P. excelsa Gaud.) syrup + 14.7 289 s p... 

Deoxy-3-0-methylfucose, D-638 6-Deoxy-3-0-methyl-D-gaJactose, F-163 6-Deoxy-3-0-methyI-L-galactose, F-163 6-Deoxy-3-O-methyl-D-glucal, D-679 6-Deoxy-3-O-methyl-L-glucal, D-679 6-Deoxy-3-0-methyl-D-glucose, D-142... 

A methylation analysis of S14, performed in the authors laboratory,44 gave 2,3,4,6-tetra-O-methyl-D-galactose, 2,4,6-tri-O-methyl-D-galactose, and 2,3,6-tri-O-methyl-D-glucose in the proportions 1 1 1. Although these are the same components as previously reported, the proportions are different. In addition to these sugars, 2-deoxy-3-0-methyl-2-(methylamino)-D-glucose was also obtained. 

A common example that has been isolated from many plant polysaccharides is 2-0-(4-0-methyl-a-D-glucopyranosyluronic acid-D-xylose (64). Hyalobiouronic acid, [2-amino-2-deoxy-3-0-(/f-D-glucopyranosyluronic acid)-D-glucose] (65), whose A-acetyl derivative is the repeating unit of... 

The structure of hyaluronic acid is now well established. Acidic hydrolysis yields the constituent disaccharide, hyalobiouronic acid, whose structure was shown to be 2-amino-2-deoxy-3-0-(P-D-glucopyranosylu-ronic acid)-D-glucose by degradative studies (W3) and, more recently, by constitutional syntheses (J7, Tl). The hexosaminidic linkage has been shown to have a pi- 4 configuration by enzyme (W4) and methylation (Hll) studies, so that hyaluronic acid may be assigned structure (1). 

Subsequently, Jeanloz and Flowers reported the synthesis of methyl hyalobiuronic acid (II.3) by condensation of l-bromo-2,3,4,6-tetra-0-acetyl-a-D-glucopy-ranoside (II.4) with II.5 in the presence of mercuric cyanide [Hg(CN)2], followed by deacetylation to produce II.6 (Scheme 5). Removal of the 4,6-O-benzylidene with acid afforded II.7, methyl 2-acetamido-2-deoxy-3-0- (j8-D-glucopyranosyl)-a-D-glu-copyranoside, in 35% yield. Attempts to selectively oxidize C6 of the D-glucose moiety in II.7 to the corresponding carboxylic acid with platinum oxide proved unsuccessful. 

Interpreted in terms of reduced electrode poisoning. Treatment of 3-0 -raethyl-D-glucose with lead hydroxide in water gave the isomeric 2-deoxy-3-Q-methyl-D-arabino-hexonic acid in the presence of sodium hydroxide, however, the products were a- and 3-gluco-meta-saccharinlc acld.- ... 

Acetamido-2-deoxy-D-mannofuranurono-6,3-lactone, A-274 2-Acetamido-2-deoxy-D-mannofuranurono-6,3-lactone, A-317 6-(2-AcetaTnido-2-deoxy-p-D-mannopyranuronosyl)-D-glucose, A-311 2-Acetamido-2-deoxy-4-0-methyl-D-glucuronic acid, A-274 2-Acetamido-5,6-di-0-acetyl-2,3-dideoxy-D-c 7iAro-hex-2-enono-l,4-lactone, A-386... 

The presence in plant materials of L-glucose, the enantiomorph of the ubiquitous D-glucose, has been reported (3) but needs confirmation. However, the natural occurrence of 2-deoxy-2-iV-methylamino-L-glucose in streptomycin and of 6-deoxy-3-0-methyl-L-glucose (L-thevetose) in certain cardiac glycosides has been established. 

Fig. 5.—Rates of Consumption142 of Lead Tetraacetate by D-Glucose and Some of its Derivatives (1) D-Glucose (approximately the same rate curve is given by the 6-O-methyl, 6-deoxy, and 5,6-carbonate derivatives), (2) 4-0-Methyl-, (3) 3-0-Methyl-, and (4) 2-0-Methyl-D-glucose.

---