Stereoselective synthesis of 1,2-cis galactosides: synthesis of a glycolipid containing Galα1-6Gal component from Zygomycetes species

Tetrahedron Letters

Volumn 47, Issue 37, 2006, Pages 6647-6650

  Hada, Noriyasu ^a   Oka, Junko ^a   Nishiyama, Ayaka ^a   Takeda, Tadahiro ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Galactosylation; 1,2 cis Glycoside; d Galactose; Di tert butylsilylene group; Zygomycetes species

Indexed keywords

4,6 O DI TERT BUTYLSILYLENE; CARBOHYDRATE DERIVATIVE; GALACTOSIDE; GLYCOLIPID; GLYCOSPHINGOLIPID; SILANE DERIVATIVE; TRISACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; BENZYLATION; CARBOHYDRATE SYNTHESIS; STEREOCHEMISTRY; ZYGOMYCETES;

ZYGOMYCETES;

EID: 33746788505     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.181     Document Type: Article

References (22)

1. Fraser-Reid B., Tatsuta K., and Thiem J. Glycoscience: Chemistry and Chemical Biology (2001), Springer
2. Toshima K., and Tatsuta K. Chem. Rev. 93 (1993) 1503-1531
3. Boons G.J. Tetrahedron 52 (1996) 1095-1121
4. Lemieux R.U., Hendriks K.B., Stick R.V., and James K. J. Am. Chem. Soc. 97 (1975) 4056-4062
5. Demchenko A., Stauch T., and Boons G.J. Synlett (1997) 818-819
6. Fukase K., Nakai Y., Kanoh T., and Kusumoto S. Synlett (1998) 84-86
7. Fukase K., Hasuoka A., Kinoshita I., and Kusumoto S. Tetrahedron 33 (1992) 7165-7168
8. Fukase K., Kinoshita I., Kanoh T., Nakai Y., Hasuoka A., and Kusumoto S. Tetrahedron 52 (1996) 3897-3904
9. Fukase K., Nakai Y., Egusa K., Porco Jr. J.A., and Kusumoto S. Synlett (1999) 1074-1078
10. Tokimoto H., Fujimoto Y., Fukase K., and Kusumoto S. Tetrahedron: Asymmetry 16 (2005) 441-447
11. Hada N., Kuroda M., and Takeda T. Chem. Pharm. Bull. 48 (2000) 1160-1165
12. Hada N., Ohtsuka I., Sugita M., and Takeda T. Tetrahedron Lett. 41 (2000) 9065-9068
13. Hada N., Sato K., and Takeda T. Chem. Pharm. Bull. 49 (2001) 1464-1467
14. Ohtsuka I., Hada N., Ohtaka H., Sugita M., and Takeda T. Chem. Pharm. Bull. 50 (2002) 600-604
15. Ohtsuka I., Hada N., Sugita M., and Takeda T. Carbohydr. Res. 337 (2003) 2037-2047
16. Yamamura T., Hada N., Kaburaki A., Yamano K., and Takeda T. Carbohydr. Res. 339 (2004) 2749-2759
17. Aoki K., Uchiyama R., Yamauchi S., Katayama T., Itonori S., Sugita M., Hada N., Hada J., Takeda T., Kumagai H., and Yamamoto K. J. Biol. Chem. 279 (2004) 32028-32034
18. Imamura A., Ando H., Korogi S., Tanabe G., Muraoka O., Ishida H., and Kiso M. Tetrahedron Lett. 44 (2003) 6725-6728
19. +: m/z 615.2577. Found: m/z 615.2570.
20. 3) δ 165.4, 165.1, 139.1, 138.4, 133.6, 133.3, 133.2, 132.6, 131.5, 130.0, 129.8, 129.7, 129.3, 129.0, 128.9, 128.8, 128.6, 128.4, 128.4, 128.3, 127.9, 127.8, 127.5, 98.5 (C-1′), 84.7 (C-1), 77.7, 76.6, 74.2, 73.9, 73.1, 71.0, 68.8, 67.8, 67.5, 67.3, 67.2, 27.7, 27.3, 23.4, 20.6.
21. 3) δ 165.5, 165.4, 165.1, 139.0, 138.4, 133.4, 133.1, 133.0, 129.9, 129.7, 129.5, 129.4, 129.1, 128.9, 128.5, 128.5, 128.3, 128.2, 127.6, 127.3, 101.1 (C-1′), 100.8 (C-1), 99.3 (C-1″), 77.6, 73.9, 73.5, 73.1, 72.2, 72.0, 71.8, 70.9, 69.8, 69.8, 68.7, 68.1, 67.9, 67.8, 67.4, 67.1, 27.6, 27.3, 23.3, 20.6, 17.6.
22. +: m/z 1048.6760. Found: m/z 1048.6793.