3,6-Anhydro-2-deoxy-D-glucose

A. B. Foster, W. G. Overend, M. Stacey, and G. Vaughan, Deoxy-sugars 25. Structure and reactivity of anhydro-sugars. 2. Derivatives of 3,6-anhydro-D-mannose, 3,6-anhydro-2-deoxy-D-galactose, and 3,6-anhydro-2-deoxy-D-glucose, J. Chem. Soc., (1954) 3367-3377. 

J. A. Serrano and E. Roman, A convenient synthesis of 3,6-anhydro-2-deoxy-D-glucose (isoglucal) and some of its derivatives, J. Carbohydr. Chem., 12 (1993) 237-246. 

Anhydro-2-deoxy-D-glucose Pteris inaequalis var. aequata Tagawa = P. excelsa Gaud.) CeHioO oil + 45.6 289 3 a z... 

I. Cerny, M. Budesinsky, T. Trnka, and M. Cerny, Preparation of 2-amino- 1,6-anhydro-2,3-dideoxy-jS-D-arabino-hexopyranose. H- and 13C-N.M.R. spectra of deoxy derivatives of 2-amino-l,6-anhydro-2-deoxy-D-glucose and 2-amino-l,6-anhydro-2-deoxy-D-mannose, Carbohydr. Res., 130 (1984) 103-114. 

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). 

Acetamido-l,5-anhydro-2-deoxy-D-mannitol, A-141 2-Acetamido-1,5-anhydro-2-deoxy-D-talitol, A-144 2-Acetamido-l,5-anhydro-3,4-di-0-benzyl-2-deoxy-D-mannitol, A-141 2-Acetamido-l,5-anhydro-3,4-di-0-benzyl-2,6-dideoxy-D-mannitol, A-149 2-Acetamido-l,5-anhydro-2,6-dideoxy-D-mannitol, A-149 2-Acetamido-l-0-benzoyl-2-deoxy-a-D-glucopyranose, A-8 2-Acetamido-l-0-benzoyl-2-deoxy-p-D-glucopyranose, A-8 2-Acetamido-3- O -benzoyl-2-deoxy-D-glucose, A-8 2-Acetamido-l-0-benzoyl-3,4,6-tri-0-benzyl-2-deoxy-a-D-glucopyraiiose, A-8... 

In another approach, 3,4-di-0-beiizyl-2-0-triflyl-l,6-anhydro-/i-D-mannopyranose (3) is treated with tetrabutyl- or tetramethylammonium fluoride in anhydrous acetonitrile, acetone, or tetrahydrofuran to yield 3,4-di-0-benzyl-2-fluoro-1.6-anhydro-2-deoxy-/TD-glucopyranose (4) as a syrup ([a]D — 28) in up to 91 % yield. With cesium fluoride in dimethylformamide only decomposition was observed in an attempted synthesis of 4 from 3. Fluoride 4 is converted into 2-fluoro-2-deoxy-D-glucose (2) in 70% yield by heating with 50% (v/v) methancsulfonic acid at 120 C for 30 minutes.t,( ... 

The first preparation of a 4,6-dimethyl ether of 2-amino-2-deoxy-D-glucose was reported by Haworth, Lake, and Peat. Action of ammonia on methyl 2,3-anhydro-4,6-di-0-methyl-j3-D-mannoside, followed by N-acetylation of the product, led to the formation of methyl 3-acetamido-3-deoxy-4,6-di-0-methyl- S-D-altroside (in high yield) and of methyl 2-acetamido-2-deoxy-4,6-di-0-methyl- S-D-glucoside (in a 9.4% yield). Methylation of the latter compound yielded a 3,4,6-trimethyl ether identical with the one prepared from natural n-glucosamine. ... 

Acetamldo-l,6-anhydro-2,3-dideoxy-B-D-rlbo-hexopyranose (76) has been synthesized from the corresponding 2-amino-2-deoxy-D-glucose... 

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