Stereoselective Synthesis of trans-2-Ethynyl-3-hydroxytetrahydropyran Derivatives

Synlett

Volumn 1996, Issue 11, 1996, Pages 1082-1084

  Alvarez, Eleuterio ^a   Pérez, Ricardo ^a   Rico, Milagros ^a   Rodríguez, Rosa Ma ^a   Suárez, Ma Candelaria ^a   Martín, Julio D ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542604592     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5681     Document Type: Article

References (17)

1. For previous studies from our group, see: Alvarez, E.; Pérez, R.; Rodríguez, R.M.; Martín, J.D. J. Org. Chem. 1996, 61, 3003.
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3. (b) Rouzand, D.; Sinaÿ, P. J.C.S., Chem. Commun. 1983, 1353.
4. (c) Giannis, A.; Sandhoff, K. Tetrahedron Lett. 1985, 26, 1479.
5. (d) Daly, S.M.; Armstrong, R.W. Tetrahedron Lens. 1989, 30, 5713.
6. (e) Sutherlin, D.P.; Armstrong, R.W. Tetrahedron Lett. 1993, 34, 4897.
7. (a) Ichikawa, Y.; Isobe, M.; Konobe, M.; Goto, T. Carbohydrate Research 1987, 171, 193,
8. (b) Isobe, M.; Tsukiyama, Y. Tetrahedron Lett. 1992, 33, 7911.
9. (c) Tsukiyama, T.; Peters, S.C.; Isobe, M. Synlett. 1993, 413.
10. (d) Hosokawa, S.; Isobe, M. Synlett. 1995, 1179.
11. (a) Tanaka, S.; Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1993, 34, 5757.
12. (b) Tanaka, S.; Isobe, M. Tetrahedron 1994, 50, 5633.
13. Nicolaou, K.C.; Hwang, C.-K.; Marron, B.E.; De Frees, S.A.; Couladouros, E.A.; Abe, Y.; Caroll, P.J.; Snyder, J.P. J. Am. Chem. Soc. 1990, 112, 3040.
14. 4 which precluded hydrolysis of the ester during the reaction process.
15. The trans-isomer 3a was synthesized via dibromoolefination of aldehyde 6 followed by treatment with 2.0 equiv of n-BuLi in THF: Corey, E.J.; Fuchs, P.L. Tetrahedron Lett. 1972, 3769.
16. 2) of 2,3,4,6-tetrabenzylglucopyranose.
17. 4NI, THF, 0°C, 12 h, 86%. For a comparative study with reported methods for synthesis of 1,6-anhydro-D-glucopyranose, see: Zottola, M.A.; Alonso, R.; Vite, G.D.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 6123, and references quoted therein.