Glucopyranose triacetate

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. 

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. 

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

The Synthesis of Alkyl-a-D Glucopyranoside from a-D-Glucopyranose-l,2-(Alkyl Orthoacetate) Triacetate. R. U. Lemieux and A. R. Morgan, IUPAC Symp. Chem. Natural Products, Kyoto, Japan, April 12-18 (1964). 

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. 

When a- or 8-D-glucopyranose pentaacetate is treated with piperidine (three molecular proportions are best), deacetylation occurs on Cl and C2, and the product is iV -(3,4,6-tri-0-acetyl-D-glucosyl)piperidine, whose structure was proved by conventional methods, including its conversion into 2-0-methyl-D-glucose. The same triacetate is obtained when piperidine reacts with 3,4,6-tri-O-acetyl-D-glucosyl chloride or with D-glucose 2,3,4,6-tetraacetate. Loss of the acetyl group on C2 must accompany or... 

Cold acetic anhydride-pyridine has been shown to give the crystalline a-triacetate with 4,6-O-ethylidene-0 -D-glucopyranose whereas previous work has given non-crystalline mixtures of a- and /3-anomers or only /3-anomer with hot acetic anhydride-sodium acetate. However, cold benzoyl chloride-pyridine gave Q ,/3-anomeric mixtures. ... 

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). 

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