Resolution of orthogonally protected myo-inositols with novozym 435 providing an enantioconvergent pathway to Ac2PIM1.
J Org Chem
; 79(22): 10916-31, 2014 Nov 21.
Article
en En
| MEDLINE
| ID: mdl-25338261
ABSTRACT
Orthogonally protected chiral myo-inositol derivatives are important intermediates for higher order myo-inositol-containing compounds. Here, the use of the immobilized enzyme Novozym 435 to efficiently catalyze the acetylation of the 5R configured enantiomer of racemic 1,2-O-isopropylidene-myo-inositols possessing chemically and sterically diverse protecting groups at O-3 and O-6 is described. The resolutions were successful with allyl, benzyl, 4-bromo-, 4-methoxy-, 4-nitro-, and 4-(3,4-dimethoxyphenyl)benzyl, propyl, and propargyl protection at O-6 in combination with either allyl or benzyl groups at O-3. Bulky protecting groups slow the rate of acetylation. No reaction was observed for 3,6-di-O-triisopropylsilyl-1,2-O-isopropylidene-myo-inositol. The utility of this methodology was demonstrated by the first reported synthesis of an Ac2PIM1 (9), which used both enantiomers of the resolved 3-O-allyl-6-O-benzyl-1,2-O-isopropylidene-myo-inositol in a convergent synthesis.
Texto completo:
1
Bases de datos:
MEDLINE
Asunto principal:
Inositol 1,4,5-Trifosfato
/
Inositol
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Lipasa
Idioma:
En
Revista:
J Org Chem
Año:
2014
Tipo del documento:
Article
País de afiliación:
Nueva Zelanda