专利号:US-9388131-B2 优先权日:2011-04-27 标题:Automated synthesis of small molecules using chiral, non-racemic boronates 发明人:BURKE MARTIN D; LI JUNQI; GILLIS ERIC P 权利人:UNIV ILLINOIS 摘要:Provided are methods for making and using chiral, non-racemic protected organoboronic acids, including pinene-derived iminodiacetic acid (PIDA) boronates, to direct and enable stereoselective synthesis of organic molecules. Also provided are methods for purifying PIDA boronates from solution. Also provided are methods for deprotection of boronic acids from their PIDA ligands. The purification and deprotection methods may be used in conjunction with methods for coupling or otherwise reacting boronic acids. Iterative cycles of deprotection, coupling, and purification can be performed to synthesize chiral, non-racemic compounds. The methods are suitable for use in an automated chemical synthesis process. Also provided is an automated small molecule synthesizer apparatus for performing automated stereoselective synthesis of chiral, non-racemic small molecules using iterative cycles of deprotection, coupling, and purification.
专利号:US-5446203-A 优先权日:1992-08-25 标题:Synthesis of haloenones and aryl or alkyl substituted enones or alkenes 发明人:MCNELIS EDWARD 权利人:UNIV NEW YORK 摘要:Alternative methods for synthesizing haloenones and haloakenes and their use as starting materials for synthesis of substituted or unsubstituted alkyl and aryl substituted enones and alkenes, including tamoxifen and tamoxifen analogs, using such haloenones and haloalkenes.
专利号:US-8053161-B2 优先权日:2006-09-25 标 题 :Resist composition, resin for use in the resist composition, compound for use in the synthesis of the resin, and pattern-forming method using the resist composition 发明人:WADA KENJI; SAEGUSA HIROSHI 权利人:FUJIFILM CORP 摘要:A resist composition comprises: (A) a resin capable of increasing its solubility in an alkali developer by action of an acid; (B) a compound capable of generating an acid upon irradiation with actinic ray or radiation; (C) a resin having at least one of a fluorine atom and a silicon atom; and (D) a solvent, wherein the resin (C) has a degree of molecular weight dispersion of 1.3 or less and a weight average molecular weight of 1.0×10 4 or less.
专利号:US-6872856-B2 优先权日:2000-06-28 标 题 :Cyclic ketones, their preparation and their use in the synthesis of amino acids 发明人:BLAKEMORE DAVID CLIVE; BRYANS JUSTIN STEPHEN 权利人:WARNER LAMBERT CO 摘要:A method is provided for making an enantiomerically pure compound of the formula: in which R and R′ represent C1 C10 alkyl, C2 C10 alkenyl or C3 C10 cycloalkyl and the wedges signify (S)- or (R)-stereochemistry, the substituents in compound (II) being trans. Conjugate addition is carried out between an organometallic nucleophile that provides a group R as defined above and (R)-4-acetoxycyclopent-2-en-1-one, (S)-4-acetoxycyclopent-2-en-1-one or a similar compound in which acetoxy is replaced by another leaving group to give, e.g. in the case of the acetoxy compound, a trans 3,4-disubstituted addition product of formula III or IV; The acetyl group is eliminated from the addition product to give an (R)- or (S)-4-alkyl or 4-alkenyl cyclopent-2-en-1-one the compound of formula is then to be hydrogenated to give a cyclopentanone of formula (I) or conjugate addition of a second organometallic nucleophile that provides a group R′ as defined above to the compound of the above formula may be carried out to give a trans 3,4-disubstituted addition product of formula (II). One of the above compounds may be converted e.g. via an intermediate (XV)-(XVIII) (in which the substituents R and R′ and the wedges have the meanings indicated above) to a gabapentin analogue of one of the formulae shown below: in which the substituents R and R′ and the wedges also have the meanings indicated above.
专利号:US-9709891-B2 优先权日:2005-12-09 标 题:Positive resist composition, resin used for the positive resist composition, compound used for synthesis of the resin and pattern forming method using the positive resist composition 发明人:KANDA HIROMI; KANNA SHINICHI 权利人:FUJIFILM CORP 摘要:A positive resist composition comprises: (A) a resin of which solubility in an alkali developer increases under an action of an acid; (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation; (C) a resin having at least one of a fluorine atom and a silicon atom; and (D) a solvent; and a pattern forming method using the positive resist composition.
专利号:US-11384044-B2 优先权日:2017-08-03 标 题 :Method for introducing substituent into α,β-unsaturated ketone and method for synthesizing prostaglandin using the same 发明人:SUZUKI MASAAKI; KOYAMA HIROKO 权利人:NAT CT GERIATRICS & GERONTOLOGY 摘要:The present invention provides a method for introducing substituents into the α-position and the β-position of an α,β-unsaturated ketone, which not only can be used for the synthesis of a prostaglandin by a three-component coupling process, but also enables synthesis of a prostaglandin in a high yield by one-pot operation without requiring the use of a large excess amount of any of the three components required for the synthesis or using a highly toxic heavy metal as a catalyst or a solvent that is highly toxic to living bodies, and a method for synthesizing a prostaglandin using the same technical means. n The method for introducing substituents into an α,β-unsaturated ketone according to the present invention is a method for introducing substituents into the carbon at the α-position and the carbon at the β-position of an α,β-unsaturated ketone, including: a first step of mixing alkyllithium and trialkylalkenyl tin in which tin atom binds to the vinyl position of the alkenyl group; a second step of mixing the mixture of the first step and dialkylzinc; a third step of mixing the mixture of the second step and an α,β-unsaturated ketone; and a fourth step of mixing the mixture of the third step and a trifluoromethanesulfonate compound.
[参考文献]: Edwin Vedejs, Et Al. A Highly Enantioselective Phosphabicyclooctane Catalyst For The Kinetic Resolution Of Benzylic Alcohols. J Am Chem Soc. 2003 Apr 9;125(14):4166-73. [参考文献]: Hiroshi Saito, Et Al. Synthesis Of Novel C-2 Substituted Vitamin D Derivatives Having Ringed Side Chains And Their Biological Evaluation On Bone. J Steroid Biochem Mol Biol. 2013 Jul:136:3-8.
合成参考文献
摘要:Zaidlewicz, M.; Pakulski, M. M., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 114. 摘要:Singh, R. P.; Deng, L., Science of Synthesis: Asymmetric Organocatalysis, (2012) 2, 53.