252001-14-2Relevant academic research and scientific papers
Ring conformations of D-glucose derivatives possessing two bulky silyl protecting groups at the 3,4-positions; the first observation of a stable full-axial chair conformer without bridge structures
Yamada, Hidetoshi,Tanigakiuchi, Koki,Nagao, Kohei,Okajima, Kotaro,Mukae, Tatsuya
, p. 5615 - 5618 (2007/10/03)
The ring conformations of 3,4-bis-O-tert-butyldimethylsilyl- and 3,4-bis-O-tert-butyldiphenylsilyl-D-glucopyranoses as well as the corresponding phenyl 1-thio-D-glucopyranosides were investigated. Observations showed that the introduction of the two tert-butyldiphenylsilyl groups can flip the pyranose-ring into the 1C4 conformation possessing more axial substituents. All the substituents of the 3,4-bis-O-tert- butyldiphenylsilyl-β-D-glucopyranose were axially oriented.
The first synthesis of herbicidin B. stereoselective construction of the tricyclic undecose moiety by a conformational restriction strategy using steric repulsion between adjacent bulky silyl protecting groups on a pyranose ring
Ichikawa, Satoshi,Shuto, Satoshi,Matsuda, Akira
, p. 10270 - 10280 (2007/10/03)
The first total synthesis of the nucleoside antibiotic herbicidin B (1b) was achieved, where a novel aldol-type C-glycosidation reaction promoted by samarium diiodide (SmI2) was used as a key step. Treatment of methyl 3,4-O-(1,1,3,3-tetraisopro
