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

70 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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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",

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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 - http://www.scopus.com/inward/record.url?scp=38749115075&partnerID=8YFLogxK

U2 - 10.1021/ol7025558

DO - 10.1021/ol7025558

M3 - Article

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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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