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

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

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 pro...

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Veröffentlicht in:Journal of organic chemistry 2004-04, Vol.69 (7), p.2634-2636
Hauptverfasser: Choi, Won Jun, Moon, Hyung Ryong, Kim, Hea Ok, Yoo, Byul Nae, Lee, Jeong A, Shin, Dae Hong, Jeong, Lak Shin
Format: Artikel
Sprache:eng
Schlagworte:
Adenosine - analogs & derivatives
Adenosine - chemistry
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Catalysis
Chemistry
Chemistry, Organic - methods
Exact sciences and technology
Molecular Structure
Nucleosides - analysis
Nucleosides - chemical synthesis
Organic chemistry
Oxidation-Reduction
Preparations and properties
Ribose - chemistry
Stereoisomerism
Structure-Activity Relationship
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0356762