First synthesis of 4′-selenonucleosides showing unusual southern conformation

Shin Jeong Lak; Dilip K. Tosh; Ok Kim Hea; Ting Wang; Xiyan Hou; Seop Yun Ho; Youngjoo Kwon; Kook Lee Sang; Jungwon Choi; Xuan Zhao Long

doi:10.1021/ol7025558

First synthesis of 4′-selenonucleosides showing unusual southern conformation

Shin Jeong Lak
, Dilip K. Tosh
, Ok Kim Hea
, Ting Wang
, Xiyan Hou
, Seop Yun Ho
, Youngjoo Kwon
, Kook Lee Sang
, Jungwon Choi
, Xuan Zhao Long

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

74 Scopus citations

Abstract

(Chemical Equation Presented) 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.

Original language	English
Pages (from-to)	209-212
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	2
DOIs	https://doi.org/10.1021/ol7025558
State	Published - 17 Jan 2008

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10.1021/ol7025558

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title = "First synthesis of 4′-selenonucleosides showing unusual southern conformation",

abstract = "(Chemical Equation Presented) 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.",

author = "Lak, \{Shin Jeong\} and Tosh, \{Dilip K.\} and Hea, \{Ok Kim\} and Ting Wang and Xiyan Hou and Ho, \{Seop Yun\} and Youngjoo Kwon and Sang, \{Kook Lee\} and Jungwon Choi and Long, \{Xuan Zhao\}",

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doi = "10.1021/ol7025558",

language = "English",

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journal = "Organic Letters",

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T1 - First synthesis of 4′-selenonucleosides showing unusual southern conformation

AU - Lak, Shin Jeong

AU - Tosh, Dilip K.

AU - Hea, Ok Kim

AU - Wang, Ting

AU - Hou, Xiyan

AU - Ho, Seop Yun

AU - Kwon, Youngjoo

AU - Sang, Kook Lee

AU - Choi, Jungwon

AU - Long, Xuan Zhao

PY - 2008/1/17

Y1 - 2008/1/17

N2 - (Chemical Equation Presented) 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.

AB - (Chemical Equation Presented) 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.

UR - https://www.scopus.com/pages/publications/38749115075

U2 - 10.1021/ol7025558

DO - 10.1021/ol7025558

M3 - Article

C2 - 18088134

AN - SCOPUS:38749115075

SN - 1523-7060

VL - 10

SP - 209

EP - 212

JO - Organic Letters

JF - Organic Letters

IS - 2

ER -

First synthesis of 4′-selenonucleosides showing unusual southern conformation

Abstract

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