10 W. G. OVEREND AND M. STACEY 



properties and reactions of the compounds thereby obtained have been 

 investigated. In particular the general chemistry of 2-deoxyribose has been 

 intensively studied. Many experiments with D-ribose have had as objective 

 the preparation in good yield of intermediates suitable for use in projected 

 syntheses of naturally occurring ribo-nucleosides and -nucleotides. Several 

 excellent reviews have been published in recent years describing the chem- 

 istry of ribose/ of sugar phosphates including the phosphoric acid esters 

 of ribose and deoxyribose^ and of ribo(and deoxyribo)-nucleosides and 

 -nucleotides.^ In addition a recent description of the chemistry of 2-deoxy- 

 sugars* includes much of interest concerning 2-deoxyribose. 



At the outset of this account attention must be directed to the nomen- 

 clature used for the class of compounds known as deoxysugars. A brief 

 perusal of the literature shows that it is extremely confusing. (See Overend 

 and Stacey^ for a full discussion of this problem.) For example, at various 

 times the sugar component of thymus nucleic acid has been referred to by 

 several different names. It is usual to name a deoxy-pentose or -hexose 

 after the parent sugar from w^hich it is prepared. The sugar moiety of 

 thymus nucleic acid can be prepared from D-ribose (I) by the glycal re- 

 action — which is used for the synthesis of 2-deoxysugars — and therefore 

 may be named 2-deoxy-D-ribose (II). However, due to the loss of asym- 



CHO CHO CHO 



HO— C— H 



I 

 H- H— C— OH 



H— C— OH 



I 

 CH2OH 



m 



metry at carbon atom 2 during this reaction, II could be prepared from 

 D-arabinose (III) by the same series of reactions, and so could equally 

 well be referred to as 2-deoxy-D-arabinose. This latter name has been pre- 

 ferred by some chemists. Recently it has become possible to prepare II 

 from D-erythrose^ • ^ without using either D-ribose or D-arabinose as an 

 intermediate, so that at first sight this system of nomenclature might 



1 R. W. Jeanloz and H. G. Fletcher, Jr., Advances in Carbohydrate Chem. 6, 135 

 (1951). 



2 L. F. Leloir, Fortschr. Chem. org. Naturstoffe 8, 47 (1951). 



3 G. W. Kenner, Fortschr. Chem. org. Naturstoffe 8, 96 (1951). 



* W. G. Overend and M. Stacey, Advances in Carbohydrate Chem. 8, 45 (1953). 



8 J. C. Sowden, J. Am. Chem. Soc. 71, 1897 (1949); 72, 808 (1950). 



6 W. G. Overend, M. Stacey, and L. F. Wiggins, J. Chem. Soc. 1949, 1358. 



