35949-66-7Relevant articles and documents
Total synthesis of spicamycin
Suzuki, Tamotsu,Suzuki, Sayaka T.,Yamada, Iwao,Koashi, Yoshiaki,Yamada, Kazue,Chida, Noritaka
, p. 2874 - 2880 (2007/10/03)
The first total synthesis of one of the spicamycin congeners, SPM VIII (3), is described. A preliminary model study for construction of the characteristic N-glycoside linkage in spicamycin using tetra-O-benzyl-β-D-mannopyranosylamine (13) and halopurines 5 revealed that Pd-catalyzed conditions successfully provided the coupling products 14 and 15 in good yields. It was also shown that thermal anomerization of the N-glycosides easily occurred, which resulted in the predominant formation of the β-anomer as the thermodynamically favored compound, and the activation energy of anomerization of 15 was estimated to be ca. 30 kcal/mol. The novel aminoheptose unit of spicamycin 6 was prepared stereoselectively by carbon elongation of an acyclic aldehyde, prepared by ring cleavage reaction of a highly functionalized cyclohexane derived from naturally abundant myo-inositol. The Pd-catalyzed coupling reaction of the β-heptopyranosylamine 6 with protected 6-chloropurine 5d, followed by deprotection, provided spicamycin amino nucleoside 2, whose condensation with dodecanoylglycine completed the total synthesis of 3. This study confirmed the proposed unique structure of a novel nucleoside antibiotic.
Synthesis and Some Properties of D-myo-Inositol 1,4,5-Tris(dihydrogen phosphate)
Ozaki, Shoichiro,Kondo, Yoshihisa,Shiotani, Naokazu,Ogasawara, Tomio,Watanabe, Yutaka
, p. 729 - 738 (2007/10/02)
Optically active myo-inositol 1,4,5-tris(dihydrogen phosphate) 1, which has now been recognized as a second messenger in a new intracellular signal transduction system, has been prepared starting from myo-inositol.The key step, phosphorylation of an adequately protected polyhydroxy derivative, was accomplished by three methods, among which a phosphoramidite method using a new phosphitylating agent, o-xylylene N,N-diethylphosphoramidite, gave the triphosphoric ester in quantitative yield.Optical resolution was effectively realized by derivatization into diastereoisomeric l-menthoxyacetic esters.NMR spectra and optical rotation are shown to depend on the pH of an aqueous solution of compound 1.
TOTAL SYNTHESIS OF OPTICALLY ACTIVE MYO-INOSITOL 1,4,5-TRIS(PHOSPHATE)
Ozaki, Shoichiro,Watanabe, Yutaka,Ogasawara, Tomio,Kondo, Yoshihisa,Shiotani, Naokazu,et al.
, p. 3157 - 3160 (2007/10/02)
Optically active myo-inositol 1,4,5-tris(phosphate) has been synthesized starting from myo-inositol.
