Synthesis of 2′-O-[(4″-O-sorboyl)-α-L-fucopyranosyl]inosine: A Shimofuridin analogue

Synlett

Volumn 1996, Issue 4, 1996, Pages 313-314

  Duynstee, Howard I ^a   Wijsman, Eric R ^a   Van Der Marel, Gijs A ^a   Van Boom, Jacques H ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343987340     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5401     Document Type: Article

References (9)

1. Kobayashi, J.; Doi, Y.; Ishibashi, M. J. Org. Chem. 1994, 59, 255.
2. Doi, Y.; Ishibashi, M.; Kobayashi, J. Tetrahedron, 1994, 50, 8651.
3. Smit, P.; De Ruiter, G.A.; van der Marel, G.A.; Rombouts, F.M.; van Boom, J.H. J. Carbohydr. Chem., 1991, 10, 833.
4. Lichtenthaler, F.W.; Sanmitsu, Y.; Norhara, T. Angew. Chem. Int. Ed. Engl., 1978, 17, 772.
5. Brown, J.M.; Cristodoulou, C.; Jones, S.S.; Modak, A.S.; Reese, C.B.; Sibanda, S.; Ubusawa, A. J. Chem. Soc. Perkin Trans. 1, 1989, 1735.
6. 5 3′,5′-silyl protected inosine derivative 3 with pivaloyloxymethyl chloride (POM-Cl).
7. 4) and concentrated. The product was purified by column chromatography (1/0 → 8/2, v/v, toluene/ethyl acetate) to give an α/β mixture of 6 in 92% yield.
8. 4) and concentrated. The residue was purified on silica gel (1/0 → 1/1, v/v, toluene/ethyl acetate) to give 7 in 53% yield.
9. Clark, J.H. Chem. Rev., 1980, 80, 429.