2,6-dideoxy sugar

Binkley, R. W., Inversion of Configuration in 2,6-Dideoxy Sugars - Triflate Displacement by Benzoate and Nitrite Anions. J. Org. Chem. 1991, 56, 3892-3896. 

In all cases, 2,6-dideoxy sugars of the d- or L-series are common and important parts of these various molecules. In general, the specific therapeutic effect is thought to be caused by the aglycone, and the sugar residue to be responsible mainly for regulating the pharmacokinetics. Thus, parameters like bioavailability, resorption, distribution, or therapeutic width are influenced by the carbohydrate moieties. By modification of the carbohydrate moiety it is, e.g., possible to enhance the efficacy of unspecific aglycones like anthracyclines or aureolic acids, or also to reduce possible side effects. Such as approach is followed in the field of class-I and -II anthracyclines in order to decrease their considerable cardiotoxicity. 

By glycosylation of 19 with the halide 20 following Helferich conditions (HgBr2, HgO), a typical but acceptable amount of the desired a-glycoside 21 (40%) of a 2,6-dideoxy sugar in the L-series was obtained which represents the A-B disaccharide unit of aclacinomycin A [8],... 

The genes involved in the biosynthesis of 2,6-dideoxy sugars have been the object of several studies.156,157... 

Highly stereocontrolled synthesis of 2,6-dideoxy sugars and its use in the synthesis of macrolide antibiotics 92YGK303. 

Tartrate esters also feature as the chiral reagents in the Sharpless asymmetric epoxidation, a reaction applied in the synthesis of deoxy-sugars. Two groups have epoxidized divinyl carbinol (33) and converted the resulting mono-epoxlde (3 ) into the 2,6-dideoxy-sugars D-ollvose (35), its 3- -niethyl ether (D-oleandrose) and 4-0 -benzyl ether, and Into D-digltoxose (36) and Its 4- -benzyl ethers (Scheme 7). Epoxidation of the meso-... 

Axenose (2,6-dideoxy-3-C-methyl-L-ji y/o-hexose) (247) has been synthesized from a 2,6-dideoxy-sugar glycoside, although the route yielded the 3-C-epimer as the principal product (Scheme 92)." Preferential formation of the /yjiri>-isomer in the Grignard reaction is unexpected in view of previous experience gained with... 

The syntheses of L-cladinose (7) and its C-3 epimer (8) have been achieved by the desulfurization of 2,6-anhydro-2-thiopyranoside derivatives (Scheme 2). A full paper on this work together with other related 2,6-dideoxy sugars has also appeared. ... 

Further interconversions of 2,6-dideoxy-sugars (Vol.20, p.79) have been reported. The triflate (32) rearranged at room temperature to the orthoester (33) which hydrolysed to give the expected mixture of D-lyxo-monobenzoates. or underwent nucleophilic displacement at C-3 to provide the D-xylo-monobenzoate (3 )... 

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