Eguchi, Tadashi published the artcileSynthesis and biological activities of 22-hydroxy and 22-methoxy derivatives of 1α,25-dihydroxyvitamin D3: importance of side chain conformation for biological activities, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Bioorganic Chemistry (1989), 17(3), 294-307, database is CAplus.
Title derivatives I (R = OH, OMe, R1 = H; R = H, R1 = OH, OMe) were prepared from 22-aldehyde II in order to clarify the precise structural requirement for exerting various biol. activities. While the synthetic vitamin D derivatives did not show any increase of serum calcium concentration in rats by oral administration, all derivatives induced into nitroblue tetrazolium (NBT)-pos. cells at a concentration more than 1 μg/mL in the NBT reduction test for induction of differentiation of HL-60 cells. The 22S-isomers I (R = H, R1 = OH, OMe) were at least 30 times more effective than the corresponding 22R-isomers I (R = OH, OMe, R1 = H). The binding affinity of I (R = H, R1 = OMe) to the chick intestinal receptor for 1α,25-dihydroxyvitamin D3 was about 3 times as potent as that of I (R = OMe, R1 = H). A major structural difference was their side chain conformations, which were elucidated by mol. mechanics calculation (MM2 force field) and NMR studies. A zig-zag conformation turned out to be sterically most favorable for 22S-isomers, whereas such a zig-zag conformation is energetically unfavorable for 22R-isomers due to the interaction between the 22-substituent and the 16-methylene group. The side chain conformation seems to be responsible for the difference of their biol. activity and the zig-zag conformation plays an important role for the activities.
Bioorganic Chemistry published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran.
Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics