Trivially Named Sugars

The trivial names are preferred for the parent sugars and for those derivatives where all stereocentres are unmodified. 

Several deoxy sugars have trivial names established by long usage, e.g. fucose (Fuc), quinovose (Qui) and rhamnose (Rha). They are illustrated here in the pyranose form. These names are retained for the unmodified sugars, but systematic names are usually preferred for the formation of names of derivatives, especially where deoxygenation is at a chiral centre of the parent sugar. (See also the alphabetical listing of trivial names in the Appendix.)... 

Carb-13.2. Names derived from trivial names of sugars... 

Note 1. The term glycal is a non-preferred, trivial name for cyclic enol ether derivatives of sugars having a double bond between carbon atoms 1 and 2 of the ring. It should not be used or modified as a class name for monosaccharide derivatives having a double bond in any other position. 

The trivial names fucitol and rhamnitol are allowed for the alditols corresponding to the 6-deoxy sugars fucose and rhamnose. 

Note, The last of the above examples is one of the possible forms of the compound referred to by the three-letter symbol Kdo (formerly the abbreviation KDO, from the previously allowed trivial name ketodeoxyoctonic acid). Similarly the symbol Kdn for the C9 sugar 3-deoxy-D-g/ycero-D-gaiacro-non-2-ulopyranosonic acid is widely used. 

A systematic nomenclature, besides correlating the above products, can remove the difficulties which have, in certain cases, been encountered on employing the trivial name of a branched-chain sugar in naming its derivatives. 7 9... 

There are numerous examples of benzopyrylium salts, benzopyransand benzopyranones, and frequently they have trivial names that reflect their long history (see Box 5.1). Many are natural products, and frequently these compounds contain hydroxy or alkoxy groups (sometimes in the form of a sugar residue). Polyhydroxylated natural products based upon 2-phenylbenzopyrylium (flavylium) salts and with ether linkages to sugars are called anthocyanins, whereas without their sugars they are known as anthocyanidins. 

H). C,8H34N206S. the first lincosaminide antibiotic to which a structure was assigned, is defined chemically as methyl 6,8-dideoxy-6-(l-methyl-fro/M-4-propyl-L-pyrrolidin-2-ylcarbonylamino)-l-thio-D-erythro-L>-gal-actu-octopyranoside. Both lincomycin and the semisynthetic clindamycin (I, R = H, R = Cl), CisH ClNjOsS, are widely used in clinical practice. The trivial name of the sugar fragment of this antibiotic, methyl a-thiolincosaminide, has lent itself to the other members of this family, whether produced as secondary metabolites of soil microorganisms or derived semisynthetically by chemical modification. 

The presence of many chiral centers in compounds of biochemical significance or natural-product interest has led to the use of stereoparents. These are parent structures having trivial names that imply (without explicitly expressing) a particular steric configuration. Common examples are the names of simple sugars, exemplified by glucose. 

Interestingly, the Beilstein Handbook (Ref. 10) used this type of labelling in the III-IV supplement, while, for supplement V, a change to sugar terms is evident. Originally, the trivial names isosorbide, isomannide, and isoidide were used in the main volume, as well as in Supplements I and II. It should, however, be pointed out that Beilstein names in supplement III-IV are based on an older stereochemical reference system according to which 3 is (3aR)-(3ar, 6ac)-hexahydrofuro-[3,2-h]furan-3c, 6f-diol. 

A different type of reduced sugar is an alditol, in which the aldehyde group of an aldose has been reduced. For example, the alditol produced from D-glucose is D-glucitol (the trivial name is sorbitol). The name of an alditol is obtained by adding -itol to the root of the name of the aldose (except for glycerol, a reduction product of glyceraldehyde). 

An organoleptic omission test on this mixture confirmed 3-hydroxy-4, 5-dimethyl-2(5H)-furanone to be the most important FIC for a raw cane sugar aroma, and the other main components in Table 1, i.e., vanillin, maltol, 4-pentyl butanolide, 4-vinyl phenol and 2,6-dimethoxy phenol, seemed to improve the overall sugary aroma. From these results, we( ) gave the trivial name sotolon" to 2-hydroxy-4,5-dimethyl-2(5H)-furanone, which is built up from "soto" (raw sugar in Japanese) and "olon" (enol lactone) as a main FIC in raw cane sugar. 

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