CAS: 2577-48-2; (S)-Methyl Pyrrolidine-2-Carboxylate

该化合物是一种活性酯衍生物,它被广泛用作有机合成和制药应用的多用途构件,其立体化学纯度(2S配置)使其对非对称合成具有价值,特别是在制作消毒器,生物活性化合物和催化剂方面;甲基酯组增强溶性和反应性,促进在温和条件下进一步实现功能化;该复合物经常用于合成基于直线的离心机和手性辅助剂,有助于对应选择性变异;其稳定性和与一系列反应条件的兼容性突出其在药用化学和精细化学生产中的效用.

结构式图片

相似化合物

2133-40-6 59936-29-7 73323-65-6

上下游产品

methanol L-prolineL-proline (S)-N-(tert-butoxycarbonyl)proline methyl ester (S)-Pyrrolidine-1,2-dicarboxylic acid 1-[2-(4-methoxy-phenyl)-2-oxo-ethyl] ester 2-methyl ester(S)-2-methoxycarbonyl-1-(2-pyridylmethyl)pyrrolidine N-(benzyloxycarbonyl)-L-leucyl-L-proline methyl ester N-[(Phenylmethoxy)carbonyl]-L-valyl-L-proline methyl ester diphenyl diselenide

合成工艺路线路线简述

    📜6-Hydroxymetatacarboline D置于盐酸,三甲基氯硅烷,水体系中,化学反应 16.0H,反应生成L-脯氨酸甲酯
    参考文献:Hr-Maldi-Ms Imaging Assisted Screening Of β-Carboline Alkaloids Discovered From Mycena Metata
    标题:Hr-Maldi-Ms Imaging Assisted Screening Of β-Carboline Alkaloids Discovered From Mycena Metata
    摘要:Fruiting Bodies Of Mycena Metata Were Screened For The Presence Of New Secondary Metabolites By Means Of HPLC-Uv,Lc-Hr-Esims,And High-Resolution Matrix-Assisted Laser Desorption/ionization Mass Spectrometry Imaging (Hr-Maldi-Ms Imaging). Thus,A New Beta-Carboline Alkaloid,6-Hydroxymetatacarboline D (1D),Was Isolated From Fruiting Bodies Of M. Metata. 6-Hydroxymetatacarboline D Consists Of A Highly Substituted Beta-Carboline Skeleton,Which Is Likely To Be Derived Biosynthetically From L-Tryptophan,2-Oxoglutaric Acid,L-Threonine,And L-Proline. The Structure Of The Alkaloid Was Established By 2D NMR Spectroscopic Methods And Hr-Esims. Moreover,By Extensive Application Of Lc-Hr-Esims,Lc-Hr-Esims/ms,And Lc-Hr-Esims3 Techniques We Were Able To Elucidate The Structures Of A Number Of Accompanying Beta-Carboline Alkaloids,1A-1C,1E-1I,And 2A-2G,Structurally Closely Related To 6-Hydroxymetatacarboline D,Which Are Present In M. Metata In Minor Amounts. The Absolute Configuration Of The Stereogenic Centers Of The Beta-Carboline Alkaloids Was Determined By Gc-Ms Comparison With Authentic Synthetic Samples After Hydrolytic Cleavage And Derivatization Of The Resulting Amino Acids.
    Doi:10.1021/np300455A

    海关参考信息

    专利信息


    专利号:US-5554725-A
    优先权日:1994-09-14
    标题:Synthesis of dolastatin 15
    发明人:PETTIT GEORGE R
    权利人:UNIV ARIZONA
    摘要:The present invention relates to the synthesis of natural (-)- dolastatin and the elucidation of the absolute configuration of this important sea hare constituent. A segment synthetic strategy was utilized for obtaining the Dolabella auricularia (Indian Ocean sea hare) depsipeptide dolastatin 15. Reaction of protected (S)-Hiva-(S)-Phe (2c) with isopropenyl chloroformate followed by Meldrum's ester, cyclization (2c→3a) of the product in toluene and finally methylation afforded the key (S)-dolapyrrolidine (Dpy) derivative (3b). Condensation of tripeptide (8) with the three unit Dpy segment (5b) followed by deprotection and coupling (diethyl phosphorocyanidate) led to dolastatin 15 in 11% overall yield. The powerful and selective activity of dolastatin 15 against the U.S. National Cancer Institute's panel of human cell lines is reported.

    专利号:US-5468876-A
    优先权日:1986-05-22
    标题:Intermediates for the stereoconservative synthesis of 1-substituted (S)-and (R)-2-aminomethylpyrrolidines
    发明人:FEDERSEL HANS-JUEGEN; HOE THOMAS; RAEMSBY STEN I; STROEM PETER H E
    权利人:ASTRA AB
    摘要:Disclosed are (R)- and (S)-isomers of the compounds of the Formulas II and III with at least 95% optical purity ##STR1## wherein R 1 and R 2 are the same or different and represent a hydrogen atom, a lower alkyl, lower alkenyl or lower alkynyl group, a cycloalkyl group or a group (CH 2 ) m Ph, wherein m is 0-3 and Ph is a substituted or unsubstituted phenyl group. n These compounds are intermediates in the stereoconservative synthesis of 1-substituted (S)- and (R)-2-aminomethylpyrrolidines.

    专利号:US-5076973-A
    优先权日:1988-10-24
    标题:Synthesis of dolastatin 3
    发明人:PETTIT GEORGE R; HOLZAPFEL CEDRIC W
    权利人:UNIV ARIZONA
    摘要:Synthesis of dolastatin 3 is accomplished by one amino acid unit addition from L-Pro-OMe employing diethyl phosphorocyanidate-triethylamine for peptide bond formation and N-Boc protection (trifluoroacetic acid cleavage). Thereafter Boc-L-Leu-L-(gln)Thz-(gly)Thz-L-Val-L-Pro-OMe was obtained, successively crystallized from ethanol-diethyl ether, converted to the OPfp active ester, Boc cleavage and cyclization in dioxane containing t-butanol and 4-pyrrolidinopyridine to yield synthetic (-)-dolastatin 3.

    专利号:US-8796454-B2
    优先权日:2012-05-04
    标 题 :Synthesis of [2.2.2]-diazabicyclic ring systems
    发明人:SCHEERER JONATHAN R
    权利人:COLLEGE WILLIAM & MARY
    摘要:Herein we describe compositions and methods for the synthesis of [2.2.2]-diazabicyclic structures comprising a domino reaction sequence involving aldol condensation, alkene isomerization, and intramolecular hetero-Diels-Alder cycloaddition. Excellent diastereofacial control during the cycloaddition is enforced with a removable chiral phenyl aminal diketopiperazine substituent. The reaction sequence rapidly generates molecular complexity and is competent with both enolizable and non-enolizable aldehyde substrates. This method provides an efficient route to [2.2.2]-diazabicyclic structures, common to bioactive prenylated indole alkaloids such as the brevianamides and stephacidins.

    专利号:WO-2024185775-A1
    优先权日:2023-03-06
    标 题:Long-chain alkenyloxy–substituted benzoyl derivative and oligonucleotide synthesis method using same
    发明人:OKADA YOHEI; INANAGA KAZATO; SHOJI Yukiya; MIZUFUNE HIDEYA; SUDO TATSUYA; ADACHI Sota; HOSOI Kazushi
    权利人:SPERA PHARMA INC; TOKYO UNIV OF AGRICULTURE AND TECHNOLOGY
    摘要:The purpose of the present invention is to provide a novel pseudo–solid phase protecting group that can be used in liquid-phase oligonucleotide synthesis. The purpose of the present invention is also to provide an oligonucleotide synthesis method that uses a novel pseudo–solid phase protecting group. The present invention provides a compound represented by formula (1) (in which R represents a C14–60 alkenyl group, n represents 2 or 3, m represents 0 or 1, p represents 1 or 2, X represents C, N, O, or S, Y represents a single bond or B(CH 2 ) t * or may form a ring with X, and Z represents a single bond or (CH 2 ) s (s being an integer from 1 to 5)). The present invention also provides an oligonucleotide production method that uses the compound.

    专利号:US-7820858-B2
    优先权日:2006-03-25
    标 题 :Concise β2-amino acid synthesis via organocatalytic aminomethylation
    发明人:CHI YONGGUI; GELLMAN SAMUEL H; POMERANTZ WILLIAM C; HORNE WILLIAM S; GUO LI; ENGLISH EMILY P
    权利人:WISCONSIN ALUMNI RES FOUND
    摘要:The present invention provides a method for the synthesis of β 2 -amino acids. The method also provides methods yielding α-substituted β-amino aldehydes and β-substituted γ-amino alcohols. The present method according to this invention allows for increased yield and easier purification using minimal chromatography or crystallization. The methods described herein are based on an aldehyde aminomethylation which involves a Mannich reaction between an aldehyde and a formaldehyde-derived N,O-acetal (iminium precursor) and a catalyst, such as, for example, L-proline or a pyrrolidine. The invention allows for large scale, commercial preparation of β 2 -amino acids.

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    合成参考文献


    摘要:Aguilar, E.; López, L. A., Science of Synthesis Knowledge Updates, (2014) 2, 9.
    摘要:Okamoto, K.; Ohe, K., Science of Synthesis Knowledge Updates, (2020) 1, 77.
    摘要:Merino, P., Science of Synthesis Knowledge Updates, (2010) 4, 325.
    摘要:Scammells, P. J., Science of Synthesis Knowledge Updates, (2013) 2, 429.
    摘要:Couve-Bonnaire, S.; Castanheiro, T.; Bouillon, J.-P., Science of Synthesis: Modern Strategies in Organofluorine Chemistry, (2025) 2.
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