Glucitol, 2-acetamido-2-deoxy-3-0-

Tsai551 has proposed a method for determining the degree of polymerization of oligosaccharides from chitin wherein they are reduced with sodium borohydride, methanolyzed, and the content of 2-acetamido-2-deoxy-D-glucitol determined as the trimethylsilyl ether. 

In another reaction sequence, compound 193 was prepared by periodate cleavage of 2-deoxy-2-(2,4-dinitroanilino)-3,4-0-isopropyli-dene-D-glucitol or 2-amino-2-deoxy-3,4-0-isopropylidene-D-glu-citol 1,2-carbamate (see Section II, 5 p. 147). Hydrolysis of the 4-acetamido-4-deoxy-1,2-0-isopropylidene-L-xylopyranose resulting (several steps), or of the N-acetyl derivative formed on treatment of 4-amino-4-deoxy-l,2-0-isopropylidene-L-xylopyranose with acetic anhydride in water, leads to the crystalline pyranose form 193. It is noteworthy that free 4-amino-4-deoxy-L-xylose, which, in alkaline solution, consists of the equilibrium mixture 101a 103a (see... 

Acetamido-5-deoxy-D-threo-pentulose and 5-acetamido-5-deoxy-L-erythro-pentulose (204) are obtainable by the bacterial oxidation of 1-acetamido-l-deoxy-D-arabinitol and 1-acetamido-l-deoxy-D-ribitol, respectively. Both ketoses are crystalline, and show a strong carbonyl vibration in their infrared spectra. Accordingly, they exist in the acyclic form. Their isopropylidene acetals are likewise acyclic. Furthermore, 5-acetamido-5,6-dideoxy-L-xylo-hexulose (205), obtainable by bacterial oxidation, shows a great tendency to assume the acyclic structure. 5-Acetamido-5-deoxy-L-xi/io-hexulose (206) may be obtained by the bacterial oxidation of 2-acetamido-2-deoxy-D-glucitol it assumes, exclusively, the sterically more-favored pyranose form. ... 

Hakamori methylation of 2-acetamido-2-deoxy-D-glucitol gave the expected N-methylacetamido-pentamethyl ether, and two minor products, the corresponding N-acetamido and N-methylpropanamido pentamethyl... 

Acetamido-3-6 -benzyl-2-deoxy-D-xylitol, A-355 2-Acetamido-2-deoxy-3,4 5,6-di-0-isopropylidene-D-glucitol, A-215 2-Acetamido-2-deoxy-D-galactitol, A-188 2-Acetamido-2-deoxy-D-glucitol, A-215 2-Acetamido-2-deoxy-D-mannitol, A-301... 

Acetamido-2-deoxy-D-galactitol, A-188 2-Acetamido-2-deoxy-D-glucitol, A-215 2-Acetamido-2-deoxy-D-mannitol, A-301... 

A micro method for determining the structures of substituted 2-acetamido-2-deoxy-D-galactitol and -glucitol in glycoproteins, etc., has been reported. Aminodeoxy[ H]alditols resulting from periodate oxidation, reduction with sodium borotritide, and hydrolysis of nmole amounts of substituted 2-acetamido-2-deoxyalditols were separated by t.l.c. and detected by autoradiography. 

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