ChemicalBook CAS DataBase List (3R,5R)-6-Cyano-3,5-dihydroxy-hexanoic Acid tert-Butyl Ester

(3R,5R)-6-Cyano-3,5-dihydroxy-hexanoic Acid tert-Butyl Ester synthesis

13synthesis methods

Product Name:(3R,5R)-6-Cyano-3,5-dihydroxy-hexanoic Acid tert-Butyl Ester
CAS Number:125971-93-9
Molecular formula:C11H19NO4
Molecular Weight:229.27

(5R)-6-Cyano-5-hydroxy-3-oxo-hexanoic Acid tert-Butyl Ester

125988-01-4
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(3R,5R)-6-Cyano-3,5-dihydroxy-hexanoic Acid tert-Butyl Ester

125971-93-9
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Yield: 90%

Reaction Conditions:

with D-glucose in water at 28; for 24 - 48 h;Microbiological reaction;

Steps:

1
Mucor cirdnelloides MTCC 5187 was maintained on Malt Extract Agar (MEA) plates prepared in sterilized MEA (5%) in distilled water.For growth in liquid medium a loopful of microbial cells was aseptically transferred from an agar plate to a 250 mL baffled conical flask containing 50 ml of medium having the following composition (per liter) - K₂ HPO₄ (1.9 g), NaH₂ PO₄.2H₂ O (2.02 g) (NH₄)₂ SO₄ (1.8 g), MgSO₄ 7H₂ O (0.2 g), FeCI₃ (0.97 mg) and trace elements solution (1 ml). Trace elements solution consisted of (per liter) CuSO₄5H₂ O (0.02 g), MnSO₄4H₂ O (0.1 g), ZnSO₄.7H₂ O (0.1 g) and CaCO₃ (1.8 g). The above minimal medium was supplemented with 0.2% (w/v) yeast extract and 2.25% (w/v) glucose.The microorganism was grown at 28⁰C on an orbital shaker at 220 rpm for 24-48 hours. Microbial cells were harvested by centrifuging at 7000 rpm for EPO 20 minutes at 10° C. The cell pellet was resuspended in 10 ml of 50 mM sodium phosphate buffer, pH 5.4 and the cells were washed by centrifuging as above. The cell pellet was finally resuspended in 10 ml of the above buffer. To the 10 ml of cell suspension in a 50 ml baffled flask glucose (10 g per liter) was added and the compound of formula IV (2 g per liter). The cells were incubated at 28 degree C on a rotary shaker at 150 rpm for 24-48 hours.The entire reaction broth was extracted with ethyl acetate. The separated ethyl acetate extracts were pooled together and dried over anhydrous sodium sulphate and the solvent removed by vacuum distillation to afford a golden oil. The extent of conversion of the compound of formula IV to the compound of formula III and the enantiomeric / diastereomeric composition of the compound of formula IV was determined by HPLC (high pressure liquid chromatography).Conversion of compound of formula III to compound of formula I was >90%.