Cyclopropanation of unsaturated sugars with ethyl diazoacetate

Tetrahedron Letters

Volumn 37, Issue 15, 1996, Pages 2533-2536

  Hoberg, John O ^a   Claffey, David J ^a  

^a NATIONAL RENEWABLE ENERGY LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; CYCLOPROPANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029983321     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00335-8     Document Type: Article

References (27)

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12. +): 431.2101, found 431.2053.
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19. Coupling constants for cyclopropane systems range between 0-6 Hz for a trans -stereochemistry, while literature values for cis -protons range between 8-10 Hz. a) Kawabata, N.; Nakagawa, T.; Nakao, T.; Yamashita, S. J. Org. Chem. 1977, 42, 3031.
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21. 2,7 = 8.8Hz (cis) (matrix presented)
22. Similar results for the cyclopropanation of disubstituted olefins and vinyl ethers with ethyl diazoacetate have been observed, see reference 4c and a) Anciaux, A. J.; Hubert, A. J.; Noels, A. F.; Petiniot, N.; Teyssie, P. J. Org. Chem. 1980, 45, 695. Recently, Horton and Fraiser-Ried published the cyclopropanation using a 5 fold excess of copper powder.
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24. For a review on the use of glycosyl bromides in synthesis see: C-Glycoside Synthesis, Postema, M H. D.; CRC press, Boca Raton, 1995.
25. 3) δ 170.6, 170.5, 169.1, 92.7, 73.5, 70.0, 61.4, 61.1, 51.9, 46.5, 36.9, 20.7, 20.6, 14.1.
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