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(3R,5S,1'R)-3-(t-butyldimethylsilyloxy)-5-hydroxy-5-(1'-phenylethoxy) pentanoic acid lactone (3R,5S,1'R)-3-(t-butyldimethylsilyloxy)-5-hydroxy-5-(1'-phenylethoxy)pentanoic acid lactone is a chiral lactone derivative synthesized via solvent-free desymmetrization of a meso-dialdehyde with chiral 1-phenylethanol, yielding high diastereoselectivity (96:4 dr). It serves as a nor-mevaldic acid surrogate and exhibits potential as a selective antifungal agent, particularly against *Botrytis cinerea*. The structure features a tetrahydro-2H-pyran-2-one core with a silyl-protected hydroxy group at the 4-position and a chiral phenylethoxy substituent at the 6-position.

459870-98-5

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459870-98-5 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 459870-98-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 4,5,9,8,7 and 0 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 459870-98:
(8*4)+(7*5)+(6*9)+(5*8)+(4*7)+(3*0)+(2*9)+(1*8)=215
215 % 10 = 5
So 459870-98-5 is a valid CAS Registry Number.

459870-98-5Downstream Products

459870-98-5Relevant articles and documents

Diastereoselective and enantioselective preparation of nor-mevaldic acid surrogates through desymmetrisation methodology. Enantioselective synthesis of (+) and (-) nor-mevalonic lactones

Botubol-Ares, José Manuel,Durán-Pe?a, María Jesús,Hernández-Galán, Rosario,Collado, Isidro G.,Harwood, Laurence M.,Macías-Sánchez, Antonio J.

, p. 7531 - 7538 (2015)

Solvent-free desymmetrisation of a meso-dialdehyde with chiral alcohols, led to preparation of 4-silyloxy-6-alkyloxytetrahydro-2H-pyran-2-one derivatives with a 96% de. This methodology, which yields the corresponding methyl nor-mevaldates with 99% ee, ha

nor-Mevaldic acid surrogates as selective antifungal agent leads against Botrytis cinerea. Enantioselective preparation of 4-hydroxy-6-(1-phenylethoxy)tetrahydro-2H-pyran-2-one

Botubol-Ares, José Manuel,Durán-Pe?a, María Jesús,Hernández-Galán, Rosario,Collado, Isidro G.,Harwood, Laurence M.,Macías-Sánchez, Antonio J.

, p. 3379 - 3387 (2015)

Abstract Solvent-free desymmetrisation of meso-dialdehyde 1 with chiral 1-phenylethan-1-ol, led to preparation of 4-silyloxy-6-alkyloxytetrahydro-2H-pyran-2-one (+)-3a with a 96:4 dr Deprotected lactone (+)-19a and the related racemic lactones 16a-18a pre

Desymmetrisation of dialdehydes: (+)-(S) and (-)-(R) nor-methyl mevaldate as versatile synthetic intermediates

Buckley, Shirley L.J.,Drew, Michael G.B.,Harwood, Laurence M.,Macías-Sánchez, Antonio J.

, p. 3593 - 3596 (2007/10/03)

Desymmetrisation of 3-(t-butyldimethylsilyloxy)pentanedial 2 may be carried out by monoacetalisation with (R)- or (S)-2-phenylethanol. The products may be elaborated to nor-methyl mevaldate derivatives.

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