170277-77-7Relevant articles and documents
Hetero Diels - Alder-biocatalysis approach for the synthesis of (S)-3-[2-{(methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methanesulfonate, a key intermediate for the synthesis of the PKC inhibitor LY333531
Caille, Jean-Claude,Govindan,Junga, Heiko,Lalonde, Jim,Yao, Yiming
, p. 471 - 476 (2002)
A cost-effective and easily scaled-up process has been developed for the synthesis of (S)-3-[2-{(methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methanesulfonate, a key intermediate used in the synthesis of a protein kinase C inhibitor drug through a combination of hetero Diels - Alder and biocatalytic reactions. The Diels - Alder reaction between ethyl glyoxylate and bntadiene was used to make racemic 2-ethoxy-carbonyl-3,6-dihydro-2H-pyran. Treatment of the racemic ester with Bacillus lentus protease resulted in the selective hydrolysis of the R-enantiomer and yielded S-2-ethoxycarbonyl-3,6-dihydro-2H-pyran in excellent optical purity, which was reduced to S-3,6-dihdro-2H-pyran-2-yl methanol. Tritylation of this alcohol, followed by reductive ozonolysis and mesylation afforded the product in 10-15% overall yield and with >99% ee and chemical purity. Details of the process development work done on each step are given.
Process for producing butanetriol derivative
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, (2008/06/13)
A process for preparing a butanetriol derivative of the formula (1) useful as intermediates of medicines wherein R1is the same defined below, which comprises reacting a compound of the formula (3) wherein R1and R2are the different protecting groups, and an ethylene glycol derivative in a basic condition to prepare a compound of the formula (4) or (4a) wherein R1and R2are the same defined above, and then subjecting the compound (4) or (4a) to selective deprotection reaction.
PROTEIN KINASE C INHIBITOR
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, (2008/06/13)
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