An unusual acetonide group migration

Tetrahedron Letters

Volumn 44, Issue 38, 2003, Pages 7201-7204

  Saksena, Anil K ^a   Girijavallabhan, Viyyoor M ^a   Puar, Mohindar S ^a   Pramanik, Birendra N ^a   Das, Pradip R ^a   McPhail, Andrew T ^b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 O ISOPROPYLIDEN 4 PENTEN 1,2,3 TRIOL MESYLATE; 3 N BENZOYLURACIL; ALCOHOL; AMIDE; MESYLIC ACID DERIVATIVE; POTASSIUM CARBONATE; UNCLASSIFIED DRUG; URACIL; URACIL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; HYDROLYSIS; MITSUNOBU REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0042009344     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01758-1     Document Type: Article

References (10)

1. Jager V., Hafele B. Synthesis. 1987;801-806.
2. 13C NMR and high-resolution mass spectra. When necessary 1D NOE and 2D NOESY NMR spectra were obtained to confirm relative stereochemistry. Elemental analysis were obtained for crystalline compounds only. Yields refer to isolated products and have not been optimized. Selective spectral data is given here.
3. 3 as eluent to yield a crystalline solid, mp 91-93°C.
4. 4) and evaporated to dryness in vacuo to provide a thick yellow oil (11.29 g) which was suitable for the next reaction.
5. 2 (150 g) column to provide in 10% n-hexane/EtOAc eluents the product 8 (2.95 g), mp 126-27°C.
6. 2. The crude product containing methyl benzoate was crystallized from EtOAc/n-hexane to provide a crystalline solid 2, mp 148-50°C.
7. 2BO).
8. 3 splitting. When a sample (∼1 mg) of the unknown dioxolane was added, the spectrum indicated an increase in the intensity of the R-(-)-10 (fast moving) component.
9. 3), 8.97 (broad).
10. Atomic parameters, bond lengths, bond angles and torsion angles for 15 have been deposited at the Cambridge Crystallographic Data Center, Cambridge, CB2 1EZ, UK. Any request should be accompanied by full literature citation for this communication.