A facile access to aryl α-sialosides: The combination of a volatile amine base and acetonitrile in glycosidation of sialosyl chlorides

Synlett

Volumn , Issue 5, 1998, Pages 479-482

  Kuboki, Atsuhito ^a   Sekiguchi, Takahiro ^a   Sugai, Takeshi ^a   Ohta, Hiromichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041665430     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1717     Document Type: Article

References (75)

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68. 26
69. D -37.3 (c, 1.10 chloroform)] in acetic acid (4 mL) was added acetyl chloride (0.4 mL) and dry HCl gas was bubbled (15-20 min) at 4 °C. The reaction flask was stoppered, and the mixture was stirred at room temperature for 3 h. In most cases, the disappearance of the starting material was confirmed within 3 h by TLC analysis. If the starting material was still observed at this stage, HCl gas was further bubbled for 2-3 min and the reaction was further continued. The workup procedure was as followed. The mixture was concentrated in vacuo. The residue was concentrated with toluene for several times to remove acetic acid. The residue was chromatographed on silica gel and the desired fractions were concentrated in vacua. The glycosyl chloride was obtained as a solid (89 mg, 93 %). This was employed in the next step without further purification. The glycosyl chloride related to KDN could be prepared in same manner. Although, starting from an anomeric mixture of peracetates, the substitution with chloride proceeds, the authors recommends the use of pure β-anomer of peracetate as the starting material. As the reaction of α-anomer is slow, the prolonged reaction until the complete disappearance of the both anomers of starting peracetates brought about the further substitution at 9-position as well as the decomposition (substitution with hydroxy group at 2-position) of desired product.
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