Morpholine sugar derivatives

Functionalized sugars and amino acids have been used to create unique morpholine scaffolds which were further elaborated to create a second generation of morpholino derivatives following the precepts of the build/couple/pair approach [73]. 

Fluorine Miscellaneous materials, 4304 Magnesium perchlorate Cellulose, etc., 4078 /V-Meth yI morpholine oxide, 1991 Nitric acid Cellulose, 4430 Perchloric acid Cellulose and derivatives, 3992 Perchloric acid Hydrofluoric acid, Structural materials, 3992 Potassium chlorate Cellulose, 4011 Potassium nitrate Cellulose, 4645 Sodium chlorate Paper, etc., or Wood, 4033 Sodium nitrate Fibrous material, 4716 Sodium nitrite Wood, 4715 Sodium peroxide Fibrous materials, 4797 Zinc permanganate Cellulose, 4705 BLEACHING POWDER Wood perchlorates Organic matter See SUGARS... 

The saturated heterocyclic rings are shown in black, and names for the most important ring types are given some (like piperidine, morpholine)you will need to remember others (tetrahydrofuran, pyrrolidine) are more obviously derived from the names for aromatic heterocycles that we wi II. discuss in the next chapter. Someef -these compounds (nicotine, coniine, cocaine) are plant products fall the class called alkaloids. Alkaloids are discussed in Chapter 51. Another important class of saturated heterocycles, sugars, will reappear rt Chapter 49. 

Further expanding upon the effects bases have on sugars, the Amadori rearrangement incorporates new nitrogen functionalities with the generation of a ketose derivative. Scheme 6.82 illustrates this reaction applied to the combination of glucose with morpholine... 

When W-aceCyl-protected sugar amines were under investigation the A -acetyl group was observed to undergo transformation to the O-benzyl imidate in competition with OH benzylation (eq 3). It appears for best yields at least 1 equiv of reagent per OH and NAc group is needed, and subsequent hydrolysis and reacetylation of the amine are necessary to obtain are the originally desired material. Similar problems were encountered with the morpholine derived lactams (eq 4), where mixed products were obtained, but with p-lactams with yV-amide protection (eq 5), t -benzylation with benzyl trichloroacetimidate proceeded smoothly. BTCA has recently been used to convert diketopiperazines into their bis-benzyl imino ethers. ... 

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