Syntheses of a partially benzylated derivative of the anhydro-d-altro-heptulose found in Coriaria japonica A and of its analogs

Tetrahedron

Volumn 64, Issue 35, 2008, Pages 8082-8088

  Matsuda, Sho ^a,b   Yamanoi, Takashi ^a   Watanabe, Mikio ^b  

^a NOGUCHI INSTITUTE   (Japan)

^b TOKAI UNIVERSITY   (Japan)

Author keywords

Anhydro d altro heptulose; Anhydrohexose; Anhydrosugar; Coriaria japonica A; Synthesis

Indexed keywords

6 ALLYL 6 HYDROXY 3,4,5 TRIS(BENZYLOXY) TETRAHYDROPYRAN 2 YLMETHYL ACETATE (6 O ACETYL 1 ALLYL 2,3,4 TRI O BENZYL DEXTRO MANNOPYRANOSE); LACTONE; MANNOHEPTULOSE; MANNOSE; PYRANOSIDE;

ARTICLE; BENZYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CORIARIA JAPONICA A; PLANT; PRIORITY JOURNAL; SYNTHESIS;

CORIARIA JAPONICA;

EID: 47049100816     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.06.068     Document Type: Article

References (16)

1. La Forge F.B., and Hudson C.S. J. Biol. Chem. 30 (1917) 61-77
2. Takenaka M., and Ono H. Tetrahedron Lett. 44 (2003) 999-1002
3. Hatano T., Yoshihara R., Hattori S., Yoshizaki M., Shingu T., and Okuda T. Chem. Pharm. Bull. 40 (1992) 1703-1710
4. Dalmas V., and Demuynck C. Tetrahedron: Asymmetry 4 (1993) 1169-1172
5. Hricoviniova-Bilikova Z., and Petrus L. Carbohydr. Res. 320 (1999) 31-36
6. Francisco C.G., Herrera A.J., and Suarez E. J. Org. Chem. 67 (2002) 7439-7445
7. Matsuda S., Matsumura K., Watanabe M., and Yamanoi T. Tetrahedron Lett. 48 (2007) 5807-5810
8. Yamanoi T., Matsumura K., Matsuda S., and Oda Y. Synlett (2005) 2973-2977
9. Ogawa T., and Nukada T. Carbohydr. Res. 136 (1985) 135-152
10. Sato K., and Yoshitomo A. Chem. Lett. (1995) 39-40 A similar steric inversion has been reported at the C-2 and C-4 positions of the d-galactopyranose derivative to form the d-mannopyranose derivative
11. Ogawa T., Nakabayashi S., and Kitajima T. Carbohydr. Res. 114 (1983) 225-236
12. Kuzuhara H., and Fletcher H.G. J. Org. Chem. 32 (1967) 2531-2534
13. Compound 15 was scarcely obtained from 14 under the reaction conditions using vinylmagnesium chloride in THF at -78 °C. It was reported that the addition of Grignard reagents to a ketone was enhanced by cerium chloride with remarkable suppression of side reactions. Imamoto T., Takiyama N., Nakamura K., Hatajima T., and Kamiya Y. J. Am. Chem. Soc. 111 (1989) 4392-4398
14. A similar conversion procedure of the 1-propenyl group of the fructofuranoside derivative into a hydroxymethyl group has been reported. Nicotra F., Panza L., and Russo G. J. Org. Chem. 52 (1987) 5627-5630
15. Adinolfi M., Iadonisi A., and Schiattarella M. Tetrahedron Lett. 44 (2003) 6479-6482
16. El-Badri M.H., Willenbring D., Tantillo D.J., and Gervay-Hague J. J. Org. Chem. 72 (2007) 4663-4672