New analogues of fosfomycin—synthesis of diethyl (1R,2R)- and (1S,2R)-1,2-epoxy-3-hydroxypropylphosphonates
✍ Scribed by Andrzej E. Wróblewski; Irena I. Bąk-Sypień
- Book ID
- 108284185
- Publisher
- Elsevier Science
- Year
- 2007
- Tongue
- English
- Weight
- 192 KB
- Volume
- 18
- Category
- Article
- ISSN
- 0957-4166
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📜 SIMILAR VOLUMES
Addition of diethyl phosphite to 2,3-O-cyclohexylidene-D-glyceraldehyde catalyzed by triethylamine or fluorides led to ca. 35:65 mixtures of diethyl (IR,2R)-and (1S,2R)-2,3-O-cyclohexylidene-l,2,3trihydroxypropylphosphonates (4a) and (4b). Application of lithium diethylphosphonate only slightly impr
The tide compounds were prepared from key intermediates readily obtained by the stereoselective Diels-Alder reaction of (Z)-2-pbenyl-4-[(S)-2,2-dimethyl-l,3dioxolan-4-ylmethylene]-5(4H)-oxazolone, a chiral az-lactone derived from (R)glyceraldehyde and cyclopentadiene.
A straightforward three step route to (1S,2R)-and (1R,2R)-[2H]-glycerols la and lb is reported. The key asymmetric step involves an AD-mix-l~ dihydroxylation on deuterium labelled Z-and E-allyl benzoates 4a and 4b. The route should facilitate the use of [2H]-glycerols la-ld in high enantiomeric puri