75857-93-1Relevant articles and documents
Hydroboration of vinylglycine and allylglycine as a route to boron- derivatives of α-amino acids
Denniel, Valerie,Bauchat, Patrick,Danion, Daniel,Danion-Bougot, Renee
, p. 5111 - 5114 (1996)
The hydroboration of protected vinylglycine and allylglycine with dicyclohexyl- or diisopinocampheylborane occurs chimio- and regioselectively with attachment of boron to the less substituted end of the carbon-carbon double bond. Homoserine or δ-hydroxynorvaline are readily obtained by H2O2/CH3CO2Na oxidation of dicyclohexylborane derivatives and 2-amino-4- boronobutanoic acid or 2-amino-5-boronopentanoic acid by reaction of diisopinocampheylborane derivatives with excess of ethanal and deprotection.
Synthesis of enkephalinase inhibitor
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Paragraph 0017, (2018/07/10)
The invention discloses a novel synthesis method of enkephalinase inhibitor Sacubitril. According to the novel synthesis method, L-Pyroglutamic acid is taken as a raw material, a plurality of steps ofreaction are carried out, and a compound I with the chirality identical to that of Sacubitril is obtained via epimerization crystallization; the compound I is subjected to acylation, and is reacted with biphenyl so as to obtain a compound II; and hydrolysis ring-opening is carried out so as to obtain a compound III; the compound III is reacted with succinic anhydride, and reduction reaction is carried out so as to obtain Sacubitril. According to the synthesis method, a novel chirality control strategy is adopted, a novel chiral center is constructed using a simple and reliable method; controlof the chiral key intermediate is carried out at the early part of the synthesis routine, so that it is beneficial for reduction of risk and cost.
SYNTHESIS OF 2-OXA AND 2-AZA ANALOGS OF PYRROLIZIDINE-3,5-DIONES (LUKES-SORM DILACTAM)
Nagasaka, Tatsuo,Hakamada, Rie,Kunii, Shin-ichi,Hamaguchi, Fumiko
, p. 619 - 630 (2007/10/02)
The synthesis of 2-oxa and 2-aza analogs of pyrrolizidine-3,5-dione (Lukes-Sorm dilactam), which has amnesia reversal activity, is reported.Optically active (+)-2-oxa and (+)-2-aza analogs and racemic 2-aza analog and its 1-methoxycarbonyl derivatives were prepared from (-)-S-pyroglutamic acid and succinimide, respectively.