Formation of the 1,2,6-orthoester of mannose and its utilization in the glycosylation reaction

Tetrahedron Letters

Volumn 40, Issue 35, 1999, Pages 6423-6426

  Hiranuma, Sayoko ^a   Kanie, Osamu ^a   Wong, Chi Huey ^a,b  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Anhydride; Glycosidation; Orthoesters; Pyridinium salts

Indexed keywords

ACID ANHYDRIDE; ESTER DERIVATIVE; MANNOSE; PYRIDINIUM DERIVATIVE;

ARTICLE; GLYCOSYLATION; SYNTHESIS;

EID: 0033609925     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01193-4     Document Type: Article

References (10)

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3. Ogawa, T.; Sasajima, K. Carbohydr. Res. 1978, 64, C3-C9.
4. Ogawa, T.; Beppu, K.; Nakabayashi, S. Carbohydr. Res. 1981, 93, C6-C9.
5. Mazurek, M.; Perlin, A. S. Can. J. Chem. 1965, 43, 1918-1923.
6. 3).
7. 4) and concentrated. Purification by column chromatography (hexane:EtOAc=5:1) afforded 3a (98 mg, 89%).
8. 4), concentrated and purified on a column of silica gel using hexane:EtOAc (3:1) as eluent. Note: 1,6-anhydro compound 9 was not observed probably due to the amount of acceptor used in the reaction (10 equivalents).
9. Polymerization of glucose 1,2,4-orthoester was reported: Nakatsubo, F.; Kamitakahara, H.; Hori, M. J. Am. Chem. Soc. 1996, 118, 1677-1681.
10. Peat, S. Adv. Carbohydr. Chem. 1946, 2, 37-77.