Convenient synthesis of methyl L-Glycero-D-Manno-heptopyranoside

Journal of Carbohydrate Chemistry

Volumn 20, Issue 2, 2001, Pages 171-180

  Yamasaki, Ryohei ^a   Takajyo, Akihiko ^c   Kubo, Hiroyuki ^b   Matsui, Takeaki ^b   Ishii, Kazuyuki ^a   Yoshida, Masashi ^a  

^a TOTTORI UNIVERSITY   (Japan)

^b Maruho Co   (Japan)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035632195     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-100103956     Document Type: Article

References (15)

1. Lüderitz, O.; Staub, A. M.; Westphal, O. Immunochemistry of O and R Antigens of Salmonella and Related Enterobacteriaceae. Bacteriol. Rev. 1966, 30 (1), 192-255.
2. Jennings, H. J.; Lugowski, C.; Ashton, F. E. The Structure of an R-Type Oligosaccharide Core Obtained from Some Lipopolysaccharides of Neisseria meningitidis. Carbohydr. Res. 1983, 121, 233-241.
3. Preston, A.; Mandrell, R. E.; Gibson, B. W.; Apicella, M. A. The Lipooligosaccharides of Pathogenic Gram-Negative Bacteria. Critical Rev. Microbiol. 1996, 22, 139-180.
4. Boons, G. J. P. H.; van der Marel, G. A.; van Boom, J. H. A Versatile and New Highly Stereoselective Approach to the Synthesis of L-Glycero-D-Manno-Heptopyrano-sides. Tetrahedron Lett. 1989, 30, 229-232.
5. Boons, G. J. P. H.; van der Marel, G. A.; Poolman, J. T.; van Boom, J. H. Synthesis of L-Glycero-α-D-Manno-Heptopyranose-Containing Disaccharide Derivatives of the Neisseria meningitidis Dephosphorylated Inner-Core Region. Recl. Trav. Chim. Pays-Bas 1989, 108, 339-343.
6. Dasser, M.; Chrétien, F.; Chapleur, Y. A Facile and Stereospecific Synthesis of L-Glycero-D-Manno-Heptose and Some Derivatives. J. Chem. Soc., Perkin Trans. 1 1990, 3091-3094.
7. Grzeszczyk, B.; Zamojski, A. Benzyl 7-O-Allyl-2,3-O-Isopropylidene-4-O-p-Methoxybenzyl-L-Glycero-α-D-Manno- Heptopyranoside, a Versatile LD-manHep Derivative. Carbohydr. Res. 1994, 262, 49-57.
8. van Delft, F. L.; van der Marel, G. A.; van Boom, J. H. [Dimethyl(phenylthiomethyl)silyl]methylmagnesium Chloride. A Novel Hydroxymethylating Reagent. Synlett. 1995, 1069-1070.
9. Hense, A.; Ley, S. V.; Osborn, H. M. I.; Owen, D. R.; Poisson, J. F.; Warriner, S. L.; Wesson, K. E. Direct Preparation of Diacetals from 1,2-Diketones and Their Use as 1,2-Diol Protecting Groups. J. Chem. Soc., Perkin Trans, 1 1997, 2023-2031.
10. Grice, P.; Ley, S. V.; Piertruszka, J.; Pripke, H. W. M.; Warriner, S. L. Preparation, Structure, Derivatization and NMR Data of Cyclohexane-1, 2-Diacetal Protected Carbohydrates. J. Chem. Soc., Perkin Trans, 1 1997, 351-363.
11. Flowers, H. M. Selective Benzylation of Some D-Galactopyranosides. Carbohydr. Res. 1982, 100, 418-423.
12. Yamasaki, R.; Bacon, B. Three-Dimensional Structural Analysis of Group B Polysaccharide of Neisseria meningitidis 6275 by Two-Dimensional (2D) NMR. Biochemistry 1991, 30, 851-857.
13. Stewart, A.; Bernlind, C.; Martin, A.; Oscarson, S.; Richards, J. C.; Schweda, E. K. H. Studies of Alkaline Mediated Phosphate Migration in Synthetic Phosphoethanolamine L-Glycero-D-Manno-Heptoside Derivatives. Carbohydr. Res. 1998, 313, 193-202.
14. Yamasaki, R.; Kerwood, D. E.; Schneider, H.; Quinn, K. P.; Griffiss, J. M.; Mandrell, R. E. The Structure of Lipooligosaccharide Produced by Neisseria gonorrhoeae, Strain 15253, Isolated from a Patient with Disseminated Infection. J. Biol. Chem. 1994, 269, 30345-30351.
15. Yamasaki, R.; Koshino, H.; Nishinaka, Y.; Kurono, S.; McQuillen, D. P.; Kume, A.; Gulati, S.; Rice, P. A. Structural and Immunochemical Characterization of a Neisseria gonorrhoeae Epitope Defined by MAb 2C7. J. Biol. Chem. 1999, 274, 36550-36558.