90661-39-5Relevant articles and documents
Total syntheses of d-allo-1-deoxynojirimycin and l-talo-1-deoxynojirimycin via reductive cyclization
Chavan, Subhash P.,Dumare, Nilesh B.,Pawar, Kailash P.
, p. 40852 - 40858 (2015/02/05)
Synthesis of a polyhydroxypiperidine framework for l-talo-1-deoxynojirimycin and d-allo-1-deoxynojirimycin was achieved from l-tartaric acid by employing flash dihydroxylation and reductive lactamisation as the key steps. This journal is
DIBAL-mediated reductive transformation of trans-dimethyl tartrate acetonide into ε-hydroxy α,β-unsaturated ester and its derivatives
Tomioka, Takashi,Yabe, Yuki,Takahashi, Tohru,Simmons, Tracy K.
, p. 4669 - 4674 (2011/07/30)
Stepwise, selective DIBAL reduction of the acetonide diester derived from tartaric acid followed by the Horner- Emmons reaction effectively provided desymmetrized hydroxy mono-olefination products in a one-pot operation.
Structure-based design, synthesis and preliminary evaluation of selective inhibitors of dihydrofolate reductase from Mycobacterium tuberculosis
El-Hamamsy, Mervat H.R.I.,Smith, Anthony W.,Thompson, Andrew S.,Threadgill, Michael D.
, p. 4552 - 4576 (2008/03/12)
Tuberculosis is an increasing threat, owing to the spread of AIDS and to the development of resistance of the causative organism, Mycobacterium tuberculosis, to the currently available drugs. Dihydrofolate reductase (DHFR) is an important enzyme of the folate cycle; inhibition of DHFR inhibits growth and causes cell death. The crystal structure of M. tuberculosis DHFR revealed a glycerol tightly bound close to the binding site for the substrate dihydrofolate; this glycerol-binding motif is absent from the human enzyme. A series of pyrimidine-2,4-diamines was designed with a two-carbon tether between a glycerol-mimicking triol and the 6-position of the heterocycle; these compounds also carried aryl substituents at the 5-position. These, their diastereoisomers, analogues lacking two hydroxy groups and analogues lacking the two-carbon spacing linker were synthesised by acylation of the anions derived from phenylacetonitriles with ethyl (4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-propanoate, ethyl (4S,5S)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-propanoate, tetrahydrooxepin-2-one and 2,3-O-isopropylidene-d-erythronolactone, respectively, to give the corresponding α-acylphenylacetonitriles. Formation of the methyl enol ethers, condensation with guanidine and deprotection gave the pyrimidine-2,4-diamines. Preliminary assay of the abilities of these compounds to inhibit the growth of TB5 Saccharomyces cerevisiae carrying the DHFR genes from M. tuberculosis, human and yeast indicated that 5-phenyl-6-((3R,4S)-3,4,5-trihydroxypentyl)pyrimidine-2,4-diamine selectively inhibited M. tuberculosis DHFR and had little effect on the human or yeast enzymes.