Nerylacetate
Nerylacetate and 1,5-dienes geranyl acetate are catalyzed to the cis-2,5-bis(hydroxymethyl)tetrahydrofurans 3 and 4 by OsO4.
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Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to
24 months(2-8C).
Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.
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The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Tetrahedron Letters, 1998 , 39 (52) :9781-4.
OsO4-Catalyzed oxidative cyclization of geranyl and neryl acetate to cis-2,5-bis(hydroxymethyl)tetrahydrofurans[Reference:
WebLink]
METHODS AND RESULTS:
OsO4 catalyzes the oxidative cyclization of the 1,5-dienes geranyl acetate (1) and Nerylacetate (2) to the cis-2,5-bis(hydroxymethyl)tetrahydrofurans 3 and 4 respectively, in the presence of NaIO4 as cooxidant in DMF. The reaction is stereospecific and proceeds with the sequential syn addition to both double bonds of the starting materials. The observed stereoselectivity can be explained by invoking the intermediacy of a square-based pyramidal osmium (VI) diester (5) that has been isolated and characterized.
CONCLUSIONS:
Evidence is reported that this substance is indeed an intermediate in the transformation of 1 to 3.
