Pyridine 5-hydroxy-2-hydroxymethyl

Chemical Name 2-Hydroxymethyl-3-hydroxy-(1-hydroxy-2-tert-butylaminoethyl)pyridine Common Name —... 

Chemical Name 3-Pyridine carboxylic acid compounded with 3,7-dihydro-7-[2-hydroxy-3-[(2-hydroxymethyl)methylamino] propyl] -1,3-dimethyl-1 H-purlne-2,6-dlone(1 1)... 

Mit neun Hydrid-Aquivalenten Diboran erhalt man als Hauptprodukt 3-Hydroxy-2-methyl-4-hydroxymethyl-pyridin-5-carbonsaure-4 -lacton2 ... 

Aus der Mutterlauge erhalt man nach Zugabe von Salzsaure 0,0129 g (14% d.Th.) 3-Hydroxy-2-methvl-4,5-bis- hydroxymethyl]-pyridin-Hydrochlorid. 

Aus Pyridoxal wird unter Erhalt der Alkohol-Gruppe 3-Hydroxy-2,4-dimethyl-5-hydroxymethyl-pyridin erhalten (s.a. S. 628)12 ... 

Unsymmetric compartmental ligands that allow for the controlled synthesis of unsymmetric Ni2 or heterobimetallic NiM complexes have received particular attention.1876,1892 A wide range of such ligands derived particularly from 2-hydroxy-3-hydroxymethyl-5-methylbenzaldehyde and 2-hydroxy-3-hydroxymethyl-bromo-benzaldehyde has now been prepared and used for Ni com-plexation. These ligands have monopodal iminic pendent arms and either mono- or dipodal aminic pendent arms and the terminal donors of the pendent arms can be provided by pyridine, imidazole, and tertiary amino groups.1893-1897 Complexes are usually prepared by reaction of the requisite Ni11 salts with the preformed ligand. 

Metabolites that contain pyridoxol (2-methyl-3-hydroxy-4,5-di[hydroxymethyl]pyridine), the water-soluble vitamin B6. Phosphorylated forms of pyridoxal (the aldehyde form) and pyridoxamine (the amino form), known respectively as pyridoxal 5-phosphate (PLP) and pyridoxamine 5-phosphate (PMP), are tightly-bound coenzymes. 

To a solution of 350 mg of methyl 4-[2-endo-hydroxy-l-exo-hydroxymethyl-3a,8b-cis-2,3,3a,8b-tetrahydro-lH-5-cyclopenta[b]benzofranyl]butyrate in 3.5 ml of anhydrous dimethylformamide cooled in an ice bath were added 140 mg of imidazole and 360 mg of t-butyldimethylsilyl chloride, and after the mixture was stirred for 3 hours at room temperature, dimethylformamide was removed under reduced pressure. The residue was dissolved in a mixture of 10 ml of acetic anhydride and 5 ml of pyridine. After the mixture was stirred for 2 hours at room temperature, the reaction mixture was concentrated. 

A solution of 1.7 g of 2-hydroxymethyl-3-benzyloxy-(l-hydroxy-2-tert-butyl-aminoethyl)pyridine in 30 ml of methanol containing 1.2 ml of water is shaken with 700 mg of 5% palladiumon-charcoal in an atmosphere of hydrogen at atmospheric pressure. In 17 minutes the theoretical amount of hydrogen has been consumed and the catalyst is filtered. Concentration of the filtrate under reduced pressure provides 1.4 g of the crude product as an oil. Ethanol (5 ml) is added to the residual oil followed by 6 ml of 1.75 N ethanolic hydrogen chloride solution and, finally, by 5 ml of isopropyl ether. The precipitated product is filtered and washed with isopropyl ether containing 20% ethanol, 1.35 g, melting point 182°C (dec.). 

Hydroxymethylation of ketone (155) was followed by protection of the aliphatic hydroxy group (2-methoxypropyl ether) and addition of an a-benzyloxymethylene group at C-4. Acidic workup at the last stage of the reaction sequence produced (156). Its transformation to aldehyde (157) was carried out by successive treatment with methoxypropyl ether, acetic anhydride and pyridine, hydrochloric acid and methanol, and finally chromic acid, pyridine and hydrochloric acid. Dehydration of (157) led to the formation of (158) in 20% yield. Reagents other than the mentioned produced appreciable quantities of the cis A/B isomer. The butenolide (159) was finally synthesized by oxidation and hydrogenolysis. In order to complete the synthesis of triptolide it was necessary to introduce the... 

Vitamin B8 (l-methyl-2-hydroxy-3,4-bis(hydroxymethyl)pyridine) E. E. Snell, Vitamins Hormones 16, 78-122 (1958). 

Cleavage of a thiazolidine ring is observed151 in the reduction of the condensation product between cysteine and pyridoxal, 2-(2-methyl - 3 - hydroxy - 5 - hydroxymethyl - 4 - pyridyl)thiazolidine - 4 -carboxylic acid (131). The reduction is best understood when the compound is considered as a derivative of 4-pyridine carbaldehyde... 

METHYL-3-HYDROXY-4,5-BIS(H DROXYMETHYL)PYRIDINE see PPK250 2-METHYL-3-HYDROXY-4,5-BIS(HYDROXYMETHYL)PYRIDINE HYDROCHLORIDE see PPK500... 

In the aldohexose series, 5-(benzylamino)-l,2-0-cyclohexylidene-5-deoxy-L-idurononitrile gives, on acid hydrolysis, an almost quantitative yield of N-benzyl-2-cyano-5-hydroxypyridinium chloride. On partial, catalytic hydrogenation of this aminonitrile, 5-(benzylamino)-I,2-0-cyclohexylidene-5-deoxy-L- do-hexodialdo-l,4-furanose is obtained. This compound is reducible with sodium borohydride to crystalline 5-(benzylamino)-l,2-0-cyclohexylidene-5-deoxy-L-idofur-anose which, on removal of the cyclohexylidene group with acid, forms the intermediate 5-(benzylamino)-5-deoxy-L-idopyranose this then loses three molecules of water per molecule, to give N-benzyl-5-hydroxy-2-(hydroxymethyl)pyridinium chloride. It is therefore clear that the transformation of 5-aminoaldoses into pyridine derivatives in acid solution is not prevented by the monoalkylation of the amino group. 

The hydroxymethyl resin and the Fmoc-protected amino acid (2 equiv) were shaken in DMF (5 mL - g resin) for 15 min at 25 °C. Pyridine (3.3 equiv) and 2,6-dichlorobenzoyl chloride (5 2 equiv) were successively added and the suspension was shaken for 15-20 h. After washing, any remaining hydroxy groups were capped as described in Section 4.3.1.3.1.1,... 

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