16749-46-5Relevant articles and documents
Improved Synthesis of 6-Deoxy-1,2-O-isopropylidene-β-L-talofuranose and 6-Deoxy-1,2-O-isopropylidene-β-L-idofuranose
Hiebl, Johann,Zbiral, Erich
, p. 691 - 695 (1990)
The key step in the preparation of 6-deoxy-1,2-O-isopropylidene-β-L-talofuranose (7) and 6-deoxy-1,2-O-isopropylidene-β-L-idofuranose (13) is the selective exchange of the 6-O-mesyl rest of 3-O-acetyl-5,6-O-dimesyl-1,2-O-isopropylidene-α-D-allofuranose (4) and 3-O-acetyl-5,6-O-dimesyl-1,2-O-isopropylidene-α-D-glucofuranose (10) by acetate group (potassium actate/18-crown-6).
Synthesis of 6-deoxy-L-idose and L-acovenose from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
Hung, Shang-Cheng,Thopate, Shankar R.,Puranik, Ramachandra
, p. 369 - 374 (2001)
A practical route toward the synthesis of 6-deoxy-L-idose and L-acovenose from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose is described. Key steps include the stereoselective hydrogenation of 6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-xylo-hex-5-enofuranose, regioselective protection of 6-deoxy-1,2-O-isopropylidene-β-L-idofuranose at O-5, and epimerisation of 6-deoxy-5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-L-idofuranose at C-3.
Conformational analysis of cyclic phosphates derived from 5-C′ substituted 1,2-O-isopropylidene-α-D-xylofuranose derivatives
Sartillo-Piscil, Fernando,Cruz, Silvano,Sánchez, Mario,H?pfl, Herbert,De Parrodi, Cecilia Anaya,Quintero, Leticia
, p. 4077 - 4083 (2007/10/03)
Twelve 2-phenoxy-2-oxo-1,3,2-dioxaphosphorinanes fused with a 1,2-O-isopropylidene-α-D-xylofuranose moiety in cis orientation and substituted at the C′5 position were prepared in two steps from commercially available diacetone-α-D-glucose. Their conformations, and configurations were determined by 1H and 31P NMR and X-ray crystallographic techniques. Both, chair-twisted-chair and chair-boat equilibria were observed in solution. We observed that the strong anisotropic shielding effect of the benzene ring in the phenoxy group generates an upfield shift of the H1 hydrogen atom, when the cyclic phosphates adopt a boat conformation. This is due to a relative cis-orientation of the P-phenoxy group and the H1 proton of the 1,2-O-isopropylidene-α-D-xylofuranose moiety. Therefore, the configuration of the phosphorus center (SP or RP) can be determined by 1H NMR spectroscopy. Interestingly, the crystal structure of one of the cyclic phosphates exhibits two independent molecules in the asymmetric unit, one with a chair and the other one with a boat conformation.