3-Deoxy-D-fructose

Condensation of 1-amino-1-deoxy-D-fructose with carbon disulfide in the presence of excess triethylamine at 5 °C, leading to a (5/ )/(5.S )-diastereo-isomeric mixture of open-chain l,3-thiazolidine-2-thiones, was reported in 1975 by Jochims (Scheme 15).39... 

Amino-1-deoxy-D-fructose acetate was reacted with dimethyl methoxymethylenemalonate in the presence of sodium carbonate in water at ambient temperature for 4 hr to give aminomethylenemalonate (19) in 97% yield several isomeric forms were present both in the solid state and in solution (86MI10) (see Table IV and Scheme 5B). 

Other sugars labeled with F that are used in PET imaging ([ F] FDGal, 2-[ F]-2-deoxytalose, l-[ F]-l-deoxy-D-fructose) are also prepared by means of nucleophilic fluorination (Figure 6.19).1-[ F]-1 -Deoxy-D-fructose cannot be used as aprobe since it... 

From Scheme 2, it may be seen that D-glucosylamine and D-fructo-sylamine are also considered to be intermediates in the formation of heterocyclic compounds. This intermediary formation of 1-amino-1-deoxy-D-fructose and D-glucosylamine from D-glucose and am-... 

Another example of the observation that the side chain attached to the anomeric carbon atom in ketoses affects the proportion of one furanose form [p. 29] is afforded by the series 1-deoxy-D-fructose JV-substituted 1-amino-... 

Four 1-amino- 1-deoxy-D-fructoses, each having a different substituent on the nitrogen atom, were studied.31 The nature of the substituent makes little difference to the composition, but, in each case, in contrast to D-fructose, there was no great preponderance of the / - over the a-furanose form in some cases, the a-furanose was preponderant. Changing the solvent from D20 to... 

Tjan SB, van den Ouweland GAM. PMR investigation into the structure of some N-substituted 1-amino-1-deoxy-D-fructoses (Amadori rearrangement products). Tetrahedron 1974 30 2891-2897. 

Razumov, A.L, Gurevich, P.A., Baigil dina, S.Y., Zykova, T.V., and Akhmadullina, A.V., 2-Phospho-rylated ethanols, Zh. Obshch. Khim., 44,459,1974 J. Gen. Chem. USSR (Engl. Transl.), 44,439, 1974. Paulsen, H., and Bartsch, W., Phosphorus-containing carbohydrates. Part 10. Reaction of carbonyl sugars with Iithio methanephosphonic esters. Preparation of dimethyl 1-deoxy-D-fructose-l-phosphonate, Chem. Ber., 108, 1229, 1975. 

The conversion of 1-amino-1-deoxy-D-fructose, isoglucosamine, to sirupy n-fructose (reported by Fischer and Tafel ) may also take place... 

Derivative of 1-deoxy-D-fructose m.p., °c. [ Jd, degrees Rotation solvent Refer- ences... 

Amino]-1 -deoxy-D-fructose, N- 1 -Deoxy-D-fiuctos-l-yl)-[amine], Af-(l-Deoxy-D-ara6mo-hexulos-l-yl)-[amine] Recommended systematic names 1 -Deoxy- l-propy lamino-D-finctose, JV-(l-deoxy-p-D-finctopyranos-l-yl)-L-alanine 16... 

Regioselective epoxide opening in l,2-anhydro-3,4 5,6-di-(9-isopropylidene-D-mannitol (46) to amine or azide constitutes another interesting synthetic pathway to D-fructosamine derivatives." As shown in Scheme 20, this reaction furnishes protected 1-amino-1-deoxy-D-mannitol derivatives 47, which can be subsequently oxidized and deprotected into respective A-substituted 1-amino-1-deoxy-D-fructose. 

A. Jakas and S. Horvat, Synthesis and NMR investigation of novel Amadori compounds (1-amino-1-deoxy-d-fructose derivatives) related to the opioid peptide, leucine-enkephalin, J. Chem. Soc. Perkin Trans. 2 (1996) 789-794. 

Reaction of 1-amino-1-deoxy-D-fructose or its iV-substituted derivatives with peracylated glycosyl isothiocyanates has led to condensation products of type 18. In the case of the ribofuranosyl compound subsequent treatment with acidic resin in ethanol gave the spironucleosides 19. ... 

Acetonation of a mixture of 1-deoxy-5,6-0-isopropylidene-D-arabino- and -D-xylo-hexulose. obtained by hydroxylation of 1,3,4-trideoxy-5,6-0-isopropylidene-D-glycero-hex-3-enulose, gave 1-deoxy-2,3 4>5-(ii-0-isopropylidene-y3-D-fructopyranose and 1 -deoxy-2,3 4,6-di-0-isopropylidene-/-D-sorbofuranose. The same two products were formed when acetonation was carried out on a mixture of 1-deoxy-D-fructose and -D-sorbose obtained from hydroxylation of 1,3,4-tri-deoxy-D-glycero-hex-3-9nulose. 

Tetra-Ac 3,4,3,6-Tetra-O-acetyl-l-chloro-1-deoxy-D-fructose Ci4Ht9C109 366.751 Cryst. (Et20/petrol). Mp 77.5-78°. 

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