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Synlett 1995; 1995(9): 925-927
DOI: 10.1055/s-1995-5120
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1,2-O-Silyl Group Rearrangements in Carbohydrates - Convenient Synthesis of Important Lactose Building Blocks1

José M. Lassaletta, Richard R. Schmidt*
  • *Fachbereich Chemie, Universität Konstanz, Postfach 5560 M 725, D-78434 Konstanz, Germany
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Publication Date:
31 December 2000 (online)

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Base dependent (1a→2a)-O- and (2a→1a)-O-silyl group rearrangements have been observed in lactose. These transformations can be employed for convenient regioselective protection or deprotection at the 2a-O-position. Thus, from readily available 6 with NaH and Bn-Br in DMF 2-O-TDS-protected benzyl lactoside 7β is directly accessible in high yield. 7β can be easily converted into 2a-O-unprotected, 2a-O-pivaloyl-protected, and 4b-O-unprotected lactose derivatives 8, 9, and 2, respectively.

1,2-O-Silyl migration, reversible - lactose, 2-O-unprotected - anomeric O-alkylation