8-O-Sialylation of neuraminic acid acceptor reactivity and anomeric stereocontrol

DOI: 10.1016/S0040-4039(97)01620-1

Source and publish data:

Tetrahedron Letters p. 6837 - 6840 (1997)

Update date:2022-08-02

Topics:

Authors:

Castro-Palomino, Julio C.

Tsvetkov, Yury E.

Schneider, Regine

Schmidt, Richard R.

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Article abstract of DOI:10.1016/S0040-4039(97)01620-1

2-O-unprotected and 2-deoxy-2,3-dehydro-neuraminic acid derivatives 2, 4, and 10 exhibit enhanced acceptor properties at their 8-hydroxy group in sialylation reactions with phosphite 5 as donor: yet, mainly (10) or exclusively (2, 4) β-glycoside bond formation was observed. The 3-phenylthionocarbonate group as stereodirecting auxiliary group in the sialyl donor 11 led with 10 as acceptor to exclusive formation of α(2-8)-linked disaccharide.

Full text of DOI:10.1016/S0040-4039(97)01620-1

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