127997-07-3

Upstream product

• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 131530-70-6 (R)-4-{[(E)-4-Methoxy-phenylimino]-methyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 127940-39-0 (S)-4-{[(E)-4-Methoxy-phenylimino]-methyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

THE FOUR-CARBON ELONGATION OF THREE-CARBON CHIRAL SYNTHONS USING 2-(TRIMETHYLSILOXY)FURAN: HIGHLY STEREOCONTROLLED ENTRY TO ENANTIOMERICALLY PURE SEVEN-CARBON α,β-UNSATURATED 2,3-DIDEOXYALDONOLACTONES

The BF3-promoted addition of 2-(trimethylsiloxy)furan to three carbon synthons derived from D- and L-glyceraldehyde, D- and L-serinal, and imines thereof furnishes C7 α,β-unsaturated 2,3-dideoxy-aldonolactone derivatives in high yield, with very high level of diastereoselection.In all the cases, compounds having 4,5-threo:5,6-erythro relative stereodisposition preferentially emerge from the reactions, accompanied by only marginal amounts of 4,5-erythro:5,6-threo epimers.An empirical rule for the rapid assignment of the configuration at C-4 (γ-carbon) of γ-substituted unsaturated and saturated β-butyrolactones is given, based upon the sign of the optical rotation values.

SYNTHESIS OF ENANTIOMERICALLY PURE 2,3-DIDEOXY-HEPT-2-ENONO-1,4-LACTONE DERIVATIVES VIA DIASTEREOSELECTIVE ADDITION OF 2-(TRIMETHYLSILOXY)FURAN TO D-GLYCERALDEHYDE AND D-SERINAL-BASED THREE-CARBON SYNTHONS

The BF3-promoted addition of 2-(trimethylsiloxy)furan to 2,3-O-isopropylidene-D-glyceraldehyde and N-t-BOC-D-serinal, and the corresponding imine derivatives gives the title seven-carbon lactones with great preference for the D-arabino diastereoisomers.