Pd-catalyzed coupling reaction of glycosylamines with 6-chloropurines: Synthesis of 6-(β-D-mannopyranosylamino)-9H-purine and its β-D-gluco isomer, N-glycoside models for spicamycin and septacidin

Tetrahedron Letters

Volumn 40, Issue 13, 1999, Pages 2573-2576

  Chida, Noritaka ^a   Suzuki, Tamotsu ^a   Tanaka, Sayaka ^a   Yamada, Iwao ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

6 (BETA GLUCOPYRANOSYLAMINO) 9H PURINE; 6 (BETA MANNOPYRANOSYLAMINO) 9H PURINE; AMINOSUGAR; GLUCOSE DERIVATIVE; GLYCOSIDE; PALLADIUM; PURINE DERIVATIVE; SEPTACIDIN; SPICAMYCIN; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR MODEL; PURINE SYNTHESIS; STREPTOMYCES;

EID: 0033605936     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00250-6     Document Type: Article

References (32)

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26. Under the reaction conditions described here, the ratio of α- and β-anomers stayed almost the same (α : β = ca. 1 : 5). Formation of the α-anomer suggested that partial anomerization of 4 might had occurred during the coupling step. A similar phenomenon has been reported by Fraser-Reid in the acylation of 4 with 2-chlorobenzoyl chloride in pyridine (α-amide and β-amide were obtained in a ratio of 1 : 4.7); see ref. 5.
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28. 2O and washed with brine, and dried. Removal of the solvent left a syrup, which was chromatographed on a column of silica gel (4 g), with EtOAc-toluene (1:3) to afford compound 6 as an anomeric mixture (α : β = ca. 1 : 5).
29. ++H), 298.1151. Found 298.1162.
30. 1H NMR of the mother liquor showed that the ratio of 8 and its α-anomer was ca. 2 : 1, implying the anomerization (α → β) had took place during the recrystallization.
31. 3, EtOH, room temp.) for long reaction time (24 h) induced the complete anomerization and provided 9 as the single β-anomer.
32. In contrast to the results obtained in the coupling of 4 with 5d, the use of (-)-BINAP significantly reduced the rate of the reaction of 9 with 5d (140 °C, 36 h), and afforded compounds 10b and 10a in lower (44 and 14%) yields.