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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

Title
Preparative and Stereoselective Synthesis of the Versatile Intermediate for Carbocyclic Nucleosides: Effects of the Bulky Protecting Groups to Enforce Facial Selectivity
Authors
Choi W.J.Moon H.R.Kim H.O.Yoo B.N.Lee J.A.Shin D.H.Jeong L.S.
Ewha Authors
정낙신
Issue Date
2004
Journal Title
Journal of Organic Chemistry
ISSN
0022-3263JCR Link
Citation
vol. 69, no. 7, pp. 2634 - 2636
Indexed
SCI; SCIE; SCOPUS WOS scopus
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.
DOI
10.1021/jo0356762
Appears in Collections:
약학대학 > 약학과 > Journal papers
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