Stereoselective synthesis of amino-substituted apio dideoxynucleosides through a distant neighboring group effect

Won Jun Choi; Hee Sung Ahn; Hea Ok Kim; Sanghee Kim; Moon Woo Chun; Lak Shin Jeong

doi:10.1016/S0040-4039(02)01295-9

Stereoselective synthesis of amino-substituted apio dideoxynucleosides through a distant neighboring group effect

Won Jun Choi
, Hee Sung Ahn
, Hea Ok Kim
, Sanghee Kim
, Moon Woo Chun
, Lak Shin Jeong

Department of Pharmacy

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

8 Scopus citations

Abstract

Novel amino-substituted apio nucleoside (2R,4R)-LJ-45 as a potential anti-HBV agent was stereoselectively synthesized from the known oxazolidine 1 through a distant neighboring group effect. It is believed that this synthetic method using a chiral template, (-)-L-serine methyl ester can be generally applied to the synthesis of other chiral amino-substituted nucleosides.

Original language	English
Pages (from-to)	6241-6243
Number of pages	3
Journal	Tetrahedron Letters
Volume	43
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4039(02)01295-9
State	Published - 26 Aug 2002

Keywords

Apio nucleoside
Distant neighboring group effect
Oxazolidine intermediate

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10.1016/S0040-4039(02)01295-9

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title = "Stereoselective synthesis of amino-substituted apio dideoxynucleosides through a distant neighboring group effect",

abstract = "Novel amino-substituted apio nucleoside (2R,4R)-LJ-45 as a potential anti-HBV agent was stereoselectively synthesized from the known oxazolidine 1 through a distant neighboring group effect. It is believed that this synthetic method using a chiral template, (-)-L-serine methyl ester can be generally applied to the synthesis of other chiral amino-substituted nucleosides.",

keywords = "Apio nucleoside, Distant neighboring group effect, Oxazolidine intermediate",

author = "Choi, \{Won Jun\} and Ahn, \{Hee Sung\} and Kim, \{Hea Ok\} and Sanghee Kim and Chun, \{Moon Woo\} and Jeong, \{Lak Shin\}",

year = "2002",

month = aug,

day = "26",

doi = "10.1016/S0040-4039(02)01295-9",

language = "English",

volume = "43",

pages = "6241--6243",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "35",

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TY - JOUR

T1 - Stereoselective synthesis of amino-substituted apio dideoxynucleosides through a distant neighboring group effect

AU - Choi, Won Jun

AU - Ahn, Hee Sung

AU - Kim, Hea Ok

AU - Kim, Sanghee

AU - Chun, Moon Woo

AU - Jeong, Lak Shin

PY - 2002/8/26

Y1 - 2002/8/26

N2 - Novel amino-substituted apio nucleoside (2R,4R)-LJ-45 as a potential anti-HBV agent was stereoselectively synthesized from the known oxazolidine 1 through a distant neighboring group effect. It is believed that this synthetic method using a chiral template, (-)-L-serine methyl ester can be generally applied to the synthesis of other chiral amino-substituted nucleosides.

AB - Novel amino-substituted apio nucleoside (2R,4R)-LJ-45 as a potential anti-HBV agent was stereoselectively synthesized from the known oxazolidine 1 through a distant neighboring group effect. It is believed that this synthetic method using a chiral template, (-)-L-serine methyl ester can be generally applied to the synthesis of other chiral amino-substituted nucleosides.

KW - Apio nucleoside

KW - Distant neighboring group effect

KW - Oxazolidine intermediate

UR - https://www.scopus.com/pages/publications/0037179158

U2 - 10.1016/S0040-4039(02)01295-9

DO - 10.1016/S0040-4039(02)01295-9

M3 - Article

AN - SCOPUS:0037179158

SN - 0040-4039

VL - 43

SP - 6241

EP - 6243

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -

Stereoselective synthesis of amino-substituted apio dideoxynucleosides through a distant neighboring group effect

Abstract

Keywords

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