Quercitol, -vibo

Synthesis of Deoxyinosamines from vibo-Quercitol. As yet, the quercitols have rarely been used as synthetic starting materials. Recently, however, Suami and Yabe (42) have reported clever syntheses of two (acetylated) deoxyinosamines (8 and 9, Y= NHAc) and one (acety-lated) deoxyinosadiamine (10, Y = NHAc) from racemic vibo-quercitol... 

The vibo or dl (124/35) quercitol (4) needed for the synthesis was prepared from rat/o-inositol (2) via the bromoquercitol (3) according to the method of McCasland and Horswill, (28). By acetonation, acetylation, deacetonation, and equatorial mesylation the mesyloxy derivative... 

A. Maras, H. Secen, Y. Sutbeyaz, and M. Balci, Convenient synthesis of (+)-ta/o-quercitol (1-deoxy-neo-inositol) and (+) vibo-quercitol (1-deoxy-myo-inositol via ene reaction of singlet oxygen, J. Org. Chem., 63 (1998) 2039-2041. 

Well known alternatives to this fractional notation are based on the use of a set of eight prefixes alio, cis, dl, epi, muco, myo, neo, and scyllo) for the inositol configurations, and of ten prefixes alio, cis, epi, gala, muco, neo, proto, scyllo, talo, and vibo) for the quercitol configurations. Since these nomenclatures, due mainly to Fletcher, Anderson and Lardy, and... 

As yet, only the (+)-proproto-quercitol (IS) is present in all of 33 species of the genus Quercus examined, and it seems to be present in every part of the tree. Nineteen plant species from eight other botanical families also contain profo-querci-tol. ... 

Mild oxidation of quercitols gives ketotetrols (or, occasionally, diketo-triols), and is achieved by the use of Acetobacter suhoxydans, - - catalytic oxygenation, or a halogen. Catalytic oxidation of mwco-quercitol is the first step in a reported synthesis of the antibiotic degradation product, 2-deoxystreptamine (better named 5-deoxystreptamine). Acetobacter studies on the cis, neo, proto, scyllo, and vibo isomers have been reported. Most halogen-oxidation products have not been well characterized. 

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