Syntheses of (1S,2S,3S,4R)- and (1R,2R,3S,4R)-2,3,4-Trihydroxycyclopentane-1-methanol, Carbocyclic Analogues of α-L-Arabinofuranose and β-D-Ribofuranose

Journal of Organic Chemistry

Volumn 54, Issue 2, 1989, Pages 276-279

  Tadano, Kin ichi ^a   Hakuba, Ken ^a   Kimura, Hiroshi ^a   Ogawa, Seiichiro ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,3,4 TRIHYDROXYCYCLOPENTANE 1 METHANOL; UNCLASSIFIED DRUG;

DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

EID: 0024548760     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00263a005     Document Type: Article

References (7)

1. This work was presented at the 56th National Meeting of the Chemical Society of Japan, Tokyo. April 1–4 1988; Abstract 3XID12.
2. Suami, T.; Tadano, K.; Kameda, Y.; Iimura, Y. Chem. Lett. 1984, 1919; J. Carbohydr. Chem. 1987, 6, 231. Suami, T.; Tadano, K.; Ueno, Y.; Fukabori, C. Chem. Lett. 1985, 1557. Tadano, K.; Ueno, Y.; Fukabori, C.; Hotta, Y.; Suami, T. Bull. Chem. Soc. Jpn. 1987, 60, 1727. Tadano, K.; Maeda, H.; Hoshino, M.; Iimura, Y.; Suami, T. Chem. Lett. 1986, 1081; J. Org. Chem. 1987, 52, 1946. Tadano, K.; Fukabori, C.; Miyazaki, M.; Kimura, H.; Suami, T. Bull. Chem. Soc. Jpn. 1987, 60, 2189. Tadano, K.; Kimura, H.; Hoshino, M.; Ogawa, S.; Suami, T. Bull. Chem. Soc. Jpn. 1987, 60, 3673. Tadano, K.; Hoshino, M.; Ogawa, S.; Suami, T. Tetrahedron Lett. 1987, 28, 2741; J. Org. Chem. 1988, 53. 1427.
3. Suhadolnik, R. J. Nucleoside Antibiotics; Wiley: New York, 1970; pp 236–245, and for related papers, see ref 2g.
4. Compounds 1, 2, and 14–20 are considered to be carbocyclic analogues of carbohydrates, which are frequently designated as pseudosugars.
5. Whistler, R. L.; Lake, W. C.; In Methods in Carbohydrate Chemistry; Whistler, R. L., BeMiller, J. N., Eds.; Academic Press: New York, 1972; Vol. VI, p 286.
6. For 1H NMR spectral interpretation of five-membered compounds, see: Jackman, L. M.; Sternhell, S. Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd ed.; Pergamon Press: Oxford, 1969; p 287.
7. Krapcho, A. P.; Jahngen, E. G. E., Jr.; Lovey, A. J.; Short, F. W. Tetrahedron Lett. 1974, 1091.