- (S)-1-Boc-3-hydroxypiperidine synthesis method
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The invention discloses a (S)-1-Boc-3-hydroxypiperidine synthesis method. The method utilizes (R)-glyceraldehyde acetonide as a raw material. Through witting reaction-based acetonitrile group addition, palladium-carbon-based double bond reduction, deprotection, p-tosyl selective addition, Raney nickel-based hydrogenation reduction of the nitrile group along with ring closing, and piperidine ring nitrogen Boc protection, the (S)-1-Boc-3-hydroxypiperidine is obtained. The method utilizes the cheap chiral raw material as a starting material, produces a chiral product and prevents large material consumption and a yield loss of a splitting technology.
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Paragraph 0062; 0063
(2016/12/01)
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- Functionalized Diorganozinc Compounds: Key Reagents for the Synthesis of Enantiomerically Pure 2,5-Disubstituted cis- and trans-Tetrahydrofurans
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1,4-Diol derivatives 4a-i were synthesized stereoselectively by either reagent- or catalyst-controlled routes using the addition of functionalized diorganozinc reagents to aldehydes.The stereoselectivities along the reagent-controlled synthetic path were in the range between 80:20 and 95:5.The stereoselectivities along the catalyst route exceeded 95:5.The 1,4-diol derivatives 4 thus obtained were transformed into enantiomerically pure cis- and trans-2,5-disubstituted tetrahydrofurans (16-20) by means of an intramolecular Williamson reaction. - Keywords: Synthesis, stereoselective / Catalysis / Tetrahydrofurans / Dialkylzinc reagents
- Berninger, Joern,Koert, Ulrich,Eisenberg-Hoehl, Christina,Knochel, Paul
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p. 1021 - 1028
(2007/10/03)
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- Total synthesis of (+)-rolliniastatin 1
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The first total synthesis of the naturally occurring acetogenin (+)-rolliniastatin 1 (1) has been achieved. A high degree of stereochemical control in the construction of the bis-THF system was accomplished by chelation controlled addition of functionalized organo-metallic reagents derived from 5 and 11 to α-alkoxy-aldehydes.
- Koert
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p. 2517 - 2520
(2007/10/02)
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- C-Nucleoside Studies. Part 21. Synthesis of Some Hydroxyalkylated Pyrrolo- and Thieno-pyrimidines Related to Known Antiviral Acyclonucleosides
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Treatment of (S)-4,5-isopropylidenedioxypentanonitrile 17 with ethyl formate and sodium hydride gave a hydroxymethylene derivative which interacted with aminoacetonitrile to give 3-cyanomethyleneamino-2-acrylonitrile 19; this was elaborated via 3-amino-2-cyano-4-pyrrol 22 into 4-amino-7-pyrrolopyrimidine 9.Treatment of the hydroxymethylene derivative of 17 with methanesulphonyl chloride, followed by acetylthioacetonitrile and sodium carbonate in ethanol gave 3-amino-2-cyano-4-thiophene 25, convertible in two steps into 4-amino-7-thienopyrimidine 10. Similar chemistry was employed for the conversion of 5,6-isopropylidenedioxyhexanonitril 30 into the higher homologues 4-amino-7-(3,4-dihydroxybutyl)pyrrolo- and thieno-(3,2-d)pyrimidine 11 and 12, and for the preparation of 4-amino-7-(4-hydroxy-3-hydroxymethylbutyl)pyrrolopyrimidine 13 from 6-benzyloxy-5-benzyloxymethylhexanonitrile 41.The hydroxyalkylated products 9-13 are C-nucleosides analogues of known antiviral agents, but did display antiviral activity.
- Buchanan, J. Grant,Craven, David A.,Wightman, Richard H.,Harnden, Michael R.
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p. 195 - 202
(2007/10/02)
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