Preparative and Stereoselective Synthesis of the Versatile Intermediate for Carbocyclic Nucleosides: Effects of the Bulky Protecting Groups to Enforce Facial Selectivity

Won Jun Choi; Hyung Ryong Moon; Hea Ok Kim; Byul Nae Yoo; Jeong A. Lee; Dae Hong Shin; Lak Shin Jeong

doi:10.1021/jo0356762

Preparative and Stereoselective Synthesis of the Versatile Intermediate for Carbocyclic Nucleosides: Effects of the Bulky Protecting Groups to Enforce Facial Selectivity

Won Jun Choi
, Hyung Ryong Moon
, Hea Ok Kim
, Byul Nae Yoo
, Jeong A. Lee
, Dae Hong Shin
, Lak Shin Jeong

Department of Pharmacy

Ewha Womans University

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

88 Scopus citations

Abstract

The preparative and stereoselective synthesis (45-50% overall yields) of the target compound 17 has been accomplished from D-ribose. The bulky protecting groups such as TBDPS and Trityl enforced the facial selectivity during Grignard reaction to give the tertiary β-allylic alcohol 16 as the sole product, which was oxidatively rearranged to the key molecule 17 in excellent yield.

Original language	English
Pages (from-to)	2634-2636
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	69
Issue number	7
DOIs	https://doi.org/10.1021/jo0356762
State	Published - 2 Apr 2004

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title = "Preparative and Stereoselective Synthesis of the Versatile Intermediate for Carbocyclic Nucleosides: Effects of the Bulky Protecting Groups to Enforce Facial Selectivity",

abstract = "The preparative and stereoselective synthesis (45-50\% overall yields) of the target compound 17 has been accomplished from D-ribose. The bulky protecting groups such as TBDPS and Trityl enforced the facial selectivity during Grignard reaction to give the tertiary β-allylic alcohol 16 as the sole product, which was oxidatively rearranged to the key molecule 17 in excellent yield.",

author = "Choi, \{Won Jun\} and Moon, \{Hyung Ryong\} and Kim, \{Hea Ok\} and Yoo, \{Byul Nae\} and Lee, \{Jeong A.\} and Shin, \{Dae Hong\} and Jeong, \{Lak Shin\}",

year = "2004",

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doi = "10.1021/jo0356762",

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T1 - Preparative and Stereoselective Synthesis of the Versatile Intermediate for Carbocyclic Nucleosides

T2 - Effects of the Bulky Protecting Groups to Enforce Facial Selectivity

AU - Choi, Won Jun

AU - Moon, Hyung Ryong

AU - Kim, Hea Ok

AU - Yoo, Byul Nae

AU - Lee, Jeong A.

AU - Shin, Dae Hong

AU - Jeong, Lak Shin

PY - 2004/4/2

Y1 - 2004/4/2

N2 - The preparative and stereoselective synthesis (45-50% overall yields) of the target compound 17 has been accomplished from D-ribose. The bulky protecting groups such as TBDPS and Trityl enforced the facial selectivity during Grignard reaction to give the tertiary β-allylic alcohol 16 as the sole product, which was oxidatively rearranged to the key molecule 17 in excellent yield.

AB - The preparative and stereoselective synthesis (45-50% overall yields) of the target compound 17 has been accomplished from D-ribose. The bulky protecting groups such as TBDPS and Trityl enforced the facial selectivity during Grignard reaction to give the tertiary β-allylic alcohol 16 as the sole product, which was oxidatively rearranged to the key molecule 17 in excellent yield.

UR - https://www.scopus.com/pages/publications/1842607464

U2 - 10.1021/jo0356762

DO - 10.1021/jo0356762

M3 - Article

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AN - SCOPUS:1842607464

SN - 0022-3263

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JF - Journal of Organic Chemistry

IS - 7

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Preparative and Stereoselective Synthesis of the Versatile Intermediate for Carbocyclic Nucleosides: Effects of the Bulky Protecting Groups to Enforce Facial Selectivity

Abstract

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