Deoxy stereoselective syntheses

Stereoselective synthesis of 3 -substituted 2 -deoxy C-nucleoside pyrazolo[l,5- ][l,3,5]triazines and their 5 -phos-phate nucleotides starting from related 3 -ketonucleosides have been accomplished <2006TL5099>. Regioselective ring closure to derivatives of the same ring system - reminiscent of those discussed in Section 11.17.5.3.5 - has been described <2006TL5441>. 

Various cis-ot,g-epoxycarbonyl compounds are stereoselectively prepared via g-bromo-g-hydroxycarbony1 compounds by application of this Sn(ll) mediated aldol reaction to a-bromocarbonyl compounds (22). Also this reaction is employed for the stereoselective synthesis of 2-amino-2-deoxy-D-arabinitol. 

S. Z. Dong and L. A. Paquette, Stereoselective synthesis of conformationally constrained 2 -deoxy-4 -thia beta-anomeric spirocyclic nucleosides featuring either hydroxyl configuration at C5, J. Org. Chem., 70 (2005) 1580-1596. 

Y. Matsumura, H. Fujii, T. Nakayama, Y. Morizawa, A. Yasuda, Titanium-promoted highly stereoselective synthesis of a,a-difluoro-, 7-dihydroxyester. Simple route to 2-deoxy-2,2-difluororibose, J. Fluor. Chem. 57 (1992) 203-207. 

J. Yoshimura and M. Matsuzawa, Stereoselective synthesis of methyl 4-C-acetyl-6-deoxy-2,3-O-methylene-D-galactonate and -D-gluconate. Determination of the D-galacto configuration of methyl eurekanate by synthesis, Carbohydr. Res. S5 C1 (1980). 

W. R. Roush, D. P. Sebesta, and R. A. James, Stereoselective synthesis of 2-deoxy-p-glycosides from glycal precursors. 2. Stereochemistry of glycosidation reactions of 2-thiophenyl- and 2-selenophenyl-a-D-g/uco-pyranosyl donors, Tetrahedron, 53 (1997) 8837-8852. 

W. R. Roush and C. E. Bennett, A highly stereoselective synthesis of 2-deoxy-P-glycosides using 2-deoxy-2-iodo-glucopyranosyl acetate donors, /. Am. Chem. Soc., 121 (1999)3541-3542. 

W. R. Roush, S. Narayan, C. E. Bennett, and K. Briner, Iodoacetoxylation of glycals stereoselective synthesis and 2-deoxy-2-iodo-a-mannopyranosyl acetates, Org. Lett., 1 (1999) 895-897. 

H. B. Mereyala and S. Guntha, Stereoselective synthesis of rare (d and l) mono and disaccharides of 5-deoxy hexofuranosiduronic acids by a facile intramolecular rearrangement of hemiacetal heptonolactone alcohols, Tetrahedron, 51 (1995) 1741-1762. 

Zhang, X. Xia, H. Dong, X. Jin, J. Meng, W.-D. Qing, F.-L. 3-Deoxy-3,3-difluoro-D-arabi-nofuranose first stereoselective synthesis and application in the preparation of gem-difluon-nated sugar nucleosides. J. Org. Chem. 2003, 68, 9026-9033. 

Lubineau, A, Le Gallic, J, Malleron, A, Stannous triflate mediated glycosidations. A stereoselective synthesis of 2-amino 2-deoxy-p-D-glucopyranosides directly with the natural A-acetyl protecting group. Tetrahedron Lett., 28, 5041-5044, 1987. 

Mereyala, H B, Kulkami, V R, Ravi, D, Sharma, G V M, Rao, B V, Reddy, G B, Stereoselective synthesis of a-linked 2-deoxysaccharides and furanosaccharides by use of 2-deoxy-2-pyridyl-1-thiopyranosides and 2-deoxy-2-pyridyl-l-thiofuranosides as donors and methyl iodide as an activator, Tetrahedron, 48, 545-562, 1992. 

Laupichler, L, Sajus, H, Thiem, J, Convenient iodonium-promoted stereoselective synthesis of 2-deoxy-a-glycosides by use of 5 -(2-deoxyglycosyl) phosphorodithioates as donors. Synthesis, 1133-1136, 1992. 

Waglund, T, Cleasson, A, Stereoselective synthesis of the a-allyl C-glycoside of 3-deoxy-D-manno-2-octulosonic acid (KDO) by use of radical chemistry, Acta Chem. Scand., 46, 73 1992. 

Mukaiyama, T, Miwa, T, Nakatsuka, T, A stereoselective synthesis of 2-amino-2-deoxy-D-arabinose and D-ribose, Chem. Lett., 145-148, 1982. 

Yamamoto, Y, Kirihata, M, Ichimoto, I, Ueda, H, Stereoselective synthesis of 2-amino-2-deoxy-D-arabinose and 2-deoxy-D-ribose, Agric. Biol. Chem., 49, 1435-1439, 1985. 

Dubreuil, D., Cleophax, J., De Almeida, M. V., Verre-Sebrie, C., Liaigre, J., Vass, G., Gero, S. D. Stereoselective synthesis of 6-deoxy and 3,6-dideoxy-D-myoinositol precursors of deoxy myoinositol phosphate analogs from D-galactose. Tetrahedron 1997, 53,16747-16766. Paquette, L. A., Kinney, M. J., Dullweber, U. Practical Synthesis of Spirocyclic Bis-C,C-glycosides. Mechanistic Models in Explanation of Rearrangement Stereoselectivity and the Bifurcation of Reaction Pathways. J. Org. Chem. 1997, 62,1713-1722. 

Molin, H., and Pring. B.G., Regio- and stereoselective synthesis of the carbocychc analogue of 3-deoxy-P-D-mann-2-octulopyranosonic acid (P-KDO) from (-)-quinic acid. Tetrahedron Lett., 26, 677, 1985. 

Matsuura, N., Yashiki, Y, Nakashima, S., Maeda, M., and Sasaki, S., A shortcut and stereoselective synthesis of l-P-alkyl-2-deoxy-D-ribose derivatives via Wittig-Horner-Emmons reaction. Heterocycles, 51, 975, 1999. 

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