ChemInform Abstract: New Building Blocks for Efficient and Highly Diastereoselective Polyol Production. Synthesis and Utility of (R′,R′,S,S) and (S′,S′,R,R)-2,3-Butane Diacetal Protected Butane Tetrol Derivatives.

✍ Scribed by Jaqueline S. Barlow; Darren J. Dixon; Alison C. Foster; Steven V. Ley; Dominic J. Reynolds

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199944157

✦ Synopsis

Butane Diacetal Protected Butane Tetrol Derivatives.

-Novel 2,3-butane diacetal-protected trihydroxybutanal (V) [and ent-(V) on analogous ways] is prepared in multigram scale starting from the corresponding protected dimethyl tartrate (I). The approach involves reduction of the diester to the corresponding diol (II), selective monosilylation and subsequent Swern oxidation of the free hydroxyl group. Aldehyde (V) undergoes highly diastereoselective Lewis acid promoted addition of allylstannanes (VI) as well as silyl enol ethers (VIII), demonstrating its synthetic usefulness in the preparation of diastereomeric polyhydroxylated compounds. -(BARLOW, JAQUELINE S.;