The expeditious preparation and reactivity of some protected forms of gluconolactones

Tetrahedron Letters

Volumn 41, Issue 15, 2000, Pages 2569-2572

  Yang, Wen Bin ^a   Tsai, Cheng Hsin ^a   Lin, Chun Hung ^a  

^a INSTITUTE OF BIOLOGICAL CHEMISTRY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; GLUCOSE; LACTONE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ESTERIFICATION; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0034620905     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00207-0     Document Type: Article

References (15)

1. De Lederkremer, R. M.; Varela, O. Adv. Carbohydr. Chem. Biochem. 1994, 50, 125-209.
2. Crawford, T. C. Adv. Carbohydr. Chem. Biochem. 1981, 38, 287-321.
3. Lundt, I. In Glycoscience, Synthesis of Substrate Analogs and Mimetics; Driguez, H.; Thiem, J., Ed.; Springer: Berlin, 1997; pp. 117-156.
4. Yoshimura, J.; Asano, K.; Umemura, K.; Horito, S.; Hashimoto, H. Carbohydr. Res. 1983, 121, 187-204.
5. Shiozaki, M. J. Org. Chem. 1991, 56, 528-532.
6. Horito, S.; Asano, K.; Umemura, K.; Hashimoto, H.; Yoshimura, J. Carbohydr. Res. 1983, 121, 175-185.
7. Plantier-Royon, R.; Anker, F. C. D. J. Carbohydr. Chem. 1991, 10, 787-811.
8. 3) δ -5.54, -5.16, -4.89, -4.81, 18.05, 25.10, 25.54, 25.56, 25.61, 26.76, 67.13, 71.67, 74.40, 75.28, 82.93, 109.44, 174.03.
9. Chittenden, G. J. F. Trav. Chim. Pays-Bas 1988, 107, 455-458.
10. 3) δ -5.47, -4.90, -3.09, -2.86, 18.01, 18.09, 20.99, 25.43, 25.79, 26.68, 45.34, 67.29, 72.85, 76.50, 79.96, 81.33, 106.08, 108.92, 117.95, 133.58, 169.20.
11. The NOESY experiment of compound 5 was carried out at -50°C. The NOESY connection was observed among H-3, H-4, and H-9. The two methyl groups of isopropylidene were also found to be spatially close to H-2 and the acetyl group. These observations indicate that the β-anomer is the reaction product. Also, the MM2 calculation suggests that the β-anomer is 1.0 kcal/mol more stable than the α-anomer.
12. 3), 1.78 (dd, 1H, J=14.1, 7.1 Hz, H-7′), 1.93 (dd, 1H, J=14.3, 6.9 Hz, H-7), 2.03 (dd, 1H, J=14.3, 4.5 Hz, H-7), 2.29 (dd, 1H, J=14.1, 4.3 Hz, H-7′), 2.42 (dd, 1H, J=4.8, 2.5 Hz, H-9), 2.50 (dd, 1H, J=4.8, 2.5 Hz, H-9′), 2.73 (t, 1H, J=4.8 Hz, H-9), 2.77 (t, 1H, J=4.8 Hz, H-9′), 3.04-3.09 (m, 2H, H-8, H-8′), 3.83-3.89 (m, 2H, H-6, H-6′), 4.02-4.09 (m, 4H, H-6, H-4, H-6′, H-4′), 4.15-4.22 (m, 4H, H-5, H-3, H-5′, H-3′), 4.96 (s, 1H, H-2′), 5.16 (s, 1H, H-2).
13. 3) δ -5.29, -5.17, -4.46, -4.32, -3.90, -3.70, -3.30, -3.18, 18.19, 18.29, 18.40, 25.73, 25.87, 26.02, 26.06, 26.12, 26.13, 26.47, 64.19, 66.47, 72.68, 73.08, 74.89, 75.42, 107.84.
14. The total synthesis of L-gulose has been accomplished starting from gluconolactone with the overall yield of 46%: Yang, W.-B.; Lin, C.-H. Chem. Commun. submitted.
15. 3) δ 20.42, 25.10, 25.19, 26.23, 26.32, 52.64, 66.46, 70.39, 70.82, 71.02, 74.18, 110.14, 167.41, 169.41, 169.46, 169.62.