Glucopyranose, 1,2-anhydro triacetate

Ci2H16Os 2,3,4-Tri-O-acety 1-1,6-anhydro-/ -D-glucopyranose (levoglu-cosan triacetate) LEVGTA 32 364... 

Anhydro-a-D-glucopyranose Triacetate, R. U. Lemieux and J. Howard, Methods Carbohydr. Chem., 2 (1963) 400-402. 

P. Brigl, Uber ein neues, das 1,2-Anhydrid der Glucose. 1,2-Anhydro-u-D-glucopyranose triacetate, Hoppe-Seyler s Z. Physiol. Chem., 122 (1922) 245-262. 

Levoglucosan (l,6-anhydro-/3-D-glucopyranose) was first isolated and characterized as its triacetate and tribenzoate by Tanret, who obtained this compound through the treatment of natural phenolic D-glucosides (picein, salicin, and coniferin) with barium hydroxide. 

Most of the acetylated monosaccharides afford the more stable anomeric fluoride in this process. However, the action of a solution of hydrogen fluoride in acetic anhydride on 1,6-anhydro-j8-D-glucopyranose triacetate (1) gave tetra-O-acetyl-jS-D-glucopyranosyl fluoride (3). This result is prob-... 

Lemieux, R U, Huber, G, A chemical synthesis of sucrose. A conformational analysis of the reactions of 1,2-anhydro-a-D-glucopyranose triacetate, J. Am. Chem. Soc., 78, 4117-4119, 1956. 

Anhydro-D-glucopyranose is obtained as its triacetate by the action of ammonia in benzene on 3,4,6-t i-0-acetyl-2-0-t ichlo oacetyl-i8-D-gluco-py anosyl chloride 53). 

---