(2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate (cas: 14431-43-7) belongs to tetrahydropyran derivatives. Tetrahydropyrans and furans principally constitute as a central motif in diverse medicinally privileged molecules. The bismuth chloride-assisted cross-cyclization between homoallylic alcohols and epoxides provided various benzyl tetrahydropyran derivatives. The reaction afforded good yields of desired products and occurred under mild conditions.COA of Formula: C6H14O7
1,4-Diazafulvenium salts was written by Behringer, Hans;Tuerck, Ulrich. And the article was included in Chemische Berichte in 1966.COA of Formula: C6H14O7 This article mentions the following:
Solutions of the appropriate I (Ar = Ph or p-MeOC6H4, Ar’ = Ph or p-Me2NC6H4) and II (Ar = Ph or p-MeOC6H4) in concentrated H2SO4 contained the corresponding 6,6-diaryl- and 6-aryl-1,4-diazafulvenium salts. The corresponding 1,4-diazafulvene was isolated in 1 case, namely III by the condensation of the appropriate aryl 2-imidazolyl ketones with Me2NPh in POCl3. p-MeOC6H4COCH2Cl (18.5 g.) in 100 cc. hot EtOH treated with 12 cc. AcOH and 13.0 g. NaN3 in 20 cc. H2O, stirred 1 hr. at 65-70° and then 4 hrs. at room temperature, refrigerated overnight, and treated with about 40 cc. H2O yielded 16.0 g. p-MeOC6H4COCH2N3 (IV), m. 68-71° (Et2O-petroleum ether). IV (16.0 g.) in 800 cc. C6H3Cl3 heated 45 min. at 200-20°, concentrated, and diluted with cyclohexane gave 8.3 g. V (Ar = p-MeOC6H4) (VI), m. 212-15° (aqueous C5H5N). p-MeC6H4COCH2Br (64 g.) in 250 cc. EtOH and 35 cc. AcOH stirred 1 day with 39 g. NaN3 in 60 cc. H2O and refrigerated 1 week gave 50 g. p-MeC6H4COCH2N3 (VII), m. 58-60°. VII (13.0 g.) in 900 cc. C6H3Cl3 heated 2 hrs. at 210-20° gave 6.3 g. V (Ar = p-MeC6H4), m. 203.5-5.5° (aqueous C5H5N). VI (1.54 g.) in 40 cc. POCl3 treated at 70° under N with 1.25 cc. Me2NPh, stirred 2 hrs. at 70°, decomposed with iced H2O, and neutralized with cooling with half-concentrated NH4OH, and the crude product chromatographed on Al2O3 gave 1-5% nearly black III, m. 172.5-3.5° (CH2Cl2-cyclohexane-ligroine). III (125 mg.) in 10 cc. C6H6 stirred 1 hr. with 0.5 millimoles PhLi-Et2O yielded VIII, m. 158-61° (aqueous EtOH). The appropriate V (0.01 mole) in dry tetrahydrofuran treated with cooling during 5 min. under N with 21 millimoles suitable aryllithium in Et2O and kept 20 hrs. at 20° gave the corresponding I. V (Ar = Ph) (IX) yielded 2.50 g. I (Ar = Ar’ = Ph) (X), m. 185-7° (aqueous EtOH). p-Me2NC6H4Li (XI) in Et2O added to VI in tetrahydrofuran gave 0.95 g. I (Ar = p-MeOC6H4, Ar’ = p-Me2NC6H4) (XII), decompose 169-71° (aqueous iso-PrOH). V (Ar = p-MeOC6H4) treated successively with 0.01 mole each MeMgI and XI gave a small amount III. XI with IX yielded 0.740 g. gray I (Ar = Ph, Ar’ = p-Me2NC6H4), decompose 166-8° (iso-PrOH-H2O). X (0.325 g.) dissolved in 8 portions in 1 cc. concentrated H2SO4 each, added dropwise with cooling to MeOH, and the combined, pale yellow solution (50 cc.) diluted with 200 cc. H2O and neutralized with cooling with half-concentrated NH4OH gave 0.21 g. XIII, m. 134-7° (aqueous EtOH). V (Ar = Ph) (2.48 g.) in 120 cc. AcOH hydrogenated 45 min. over 1 g. Pd-CO yielded 1.57 g. II (Ar = Ph), m. 112-15° (MeNO2). VI (7.7 g.) in 150 cc. AcOH hydrogenated over 2. g. Pd-C gave 5.5 g. II (Ar = p-MeOC6H4), m. 170-2° (MeCN). The uv spectra of III and XII are recorded. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate (cas: 14431-43-7COA of Formula: C6H14O7).
(2S,3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol hydrate (cas: 14431-43-7) belongs to tetrahydropyran derivatives. Tetrahydropyrans and furans principally constitute as a central motif in diverse medicinally privileged molecules. The bismuth chloride-assisted cross-cyclization between homoallylic alcohols and epoxides provided various benzyl tetrahydropyran derivatives. The reaction afforded good yields of desired products and occurred under mild conditions.COA of Formula: C6H14O7
Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics