First synthesis of 4'-selenonucleosides showing unusual Southern conformation.
The first synthesis of 4'-selenonucleosides was achieved using a Pummerer-type condensation as a key step. All stereoelectronic effects shown in 4'-oxonucleosides were overwhelmed by the size of selenium and steric interactions, driving the conformation to the C2'-endo/ C3'-exo twist (Southern) conformation.
Jeong
Lak Shin
LS
Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, Korea. lakjeong@ewha.ac.kr
Tosh
Dilip K
DK
Kim
Hea Ok
HO
Wang
Ting
T
Hou
Xiyan
X
Yun
Ho Seop
HS
Kwon
Youngjoo
Y
Lee
Sang Kook
SK
Choi
Jungwon
J
Zhao
Long Xuan
LX
D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D009705:Nucleosides; D016566:Organoselenium Compounds