CAS: 132201-33-3; N-Benzoyl-(2R,3S)-3-Phenylisoserine

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CAS号136561-53-0 (2R,3S)-3-苯基异丝胺酸 | CAS号98-88-4 苯甲酰氯 | CAS号153433-80-8 (2R,3S)-3-(苯甲酰基... | CAS号32981-85-4 (2R,3S)-3-苯甲酰氨基... | CAS号860646-95-3 ethyl (2R,3S)-3... | CAS号201804-27-5 (2R,3S)-tert-bu... | CAS号132201-32-2 (2R,3S)-3-苯基异丝氨酸盐酸盐 | CAS号100-52-7 苯甲醛 | CAS号136693-04-4 N-[(1S,2S)-2-(1... | CAS号33069-62-4 紫杉醇 | CAS号32981-85-4 (2R,3S)-3-苯甲酰氨基...

合成工艺路线路线简述

    📜Methyl Cinnamate置于palladium On Activated Charcoal 盐酸,Sodium Hydroxide,Sodium Azide,N-甲基吲哚酮,Hydroquinone 1,4-Phthalazinediyl Diether,Potassium Dioxotetrahydroxoosmate(Vi),乙酰溴,氢气,对甲苯磺酸体系中,用 甲醇,二氯甲烷,水,N,N-二甲基甲酰胺,叔丁醇 用作溶剂,-15.0~50.0 °C,101.33 Kpa 条件下,反应 83.0H,反应生成N-苯甲酰基-(2R,3S)-3-苯基异丝氨酸
    参考文献:Large-Scale And Highly Enantioselective Synthesis Of The Taxol C-13 Side Chain Through Asymmetric Dihydroxylation
    标题:Large-Scale And Highly Enantioselective Synthesis Of The Taxol C-13 Side Chain Through Asymmetric Dihydroxylation
    摘要:
    Doi:10.1021/jo00096A072

    海关参考信息

    专利信息


    专利号:US-7893283-B2
    优先权日:2004-06-04
    标题:Semi-synthesis of taxane intermediates and their conversion to paclitaxel and docetaxel
    发明人:NAIDU RAGINA
    权利人:CHATHAM BIOTEC LTD
    摘要:A process is provided for the semi-synthesis of taxane intermediates useful in the preparation of paclitaxel and docetaxel, in particular, the semi-synthesis of protected taxane intermediates.

    专利号:US-7838694-B2
    优先权日:2004-04-23
    标题 :Semi-synthesis and isolation of taxane intermediates from a mixture of taxanes
    发明人:NAIDU RAGINA; FOO SAMUEL SIANG KIANG
    权利人:CHATHAM BIOTEC LTD
    摘要:A process is provided for the semi-synthesis and isolation of taxane intermediates useful in the preparation of paclitaxel and docetaxel, in particular, the semi-synthesis and isolation of 10-deacetylbaccatin III, the semi-synthesis of a mixture of 10-deacetylbaccatin III and baccatin III, and protected derivatives thereof, from a mixture of taxanes.

    专利号:US-2001041803-A1
    优先权日:2000-03-21
    标题 :Conversion of 9-dihydro-13-acetylbaccatin III to baccatin III and 10-deacetyl baccatin III
    发明人:KASITU GERTRUDE C; NOAH JAPHETH W
    摘要:Novel methods and synthetic intermediates to prepare baccatin III and 10-deacetylbaccatin from readily available 9-dihydro-13-acetylbaccatin III are described. Selective protection and deprotection of the C-7 hydroxyl functionality provides an entry into facile synthesis of novel taxol intermediates, as well as, providing new methods for the preparation of paclitaxel and docetaxel in large scale. Selective oxidation of the C-9 hydroxyl without the need for protection of the C-7 hydroxyl is described.

    专利号:US-6509506-B1
    优先权日:1997-05-21
    标 题 :Two step synthesis of D- and L- α-amino acids and D- and L- α-amino aldehydes
    发明人:SHARPLESS K BARRY; LI GUIGEN
    权利人:SCRIPPS RESEARCH INST
    摘要:D- and L- α-amino acids and D- and L-α-amino aldehydes are synthesized from olefin substrates in two steps. The first step is a catalyzed asymmetric aminohydroxylation addition reaction to the olefin substrate. The addition reaction is catalyzed by osmium and is co-catalyzed by chiral ligands. The chiral ligands, in addition to being co-catalysts with the osmium, also serve to direct the addition reaction regioselectively and enantioselectively, divalent ligands are preferred over monovalent ligands because of their enhanced regio-and enantio-selectivity. As an oxidant nitrogen source for the addition reaction, either a carbamate or sulfonamide may be employed. If carbamate is employed as an oxidant nitrogen source, the resultant β-hydoxycarbamate is deprotected to yield the corresponding β-hydroxyamine. If sulfonamide is employed as an oxidant nitrogen source, the resultant β-hydroxysulfonamide is deprotected to yield the corresponding β-hydroxyamine. The resultant β-hydroxyamine is then selectively oxidized in a second synthetic step to produce the desired D- and L- α-amino acid or D- and L-α-amino aldehyde.

    专利号:US-8106231-B2
    优先权日:2007-02-22
    标 题 :Process for the preparation of (2R,3S)-3-phenylisoserine methyl ester acetate salt
    发明人:CICERI DANIELE; GABETTA BRUNO; VIGNOLA NICOLA; MITZEL FRIEDER; WEBER BEAT T
    权利人:CICERI DANIELE; GABETTA BRUNO; VIGNOLA NICOLA; MITZEL FRIEDER; WEBER BEAT T; INDENA SPA
    摘要:A process for the enantioselective preparation of (2R,3S)-3-phenylisoserine methyl ester acetate salt of formula (I) which is an useful building block for the synthesis of taxane derivatives. The process involves the resolution of racemic threo-phenylisoserine amide and its conversion into (I).

    专利号:US-7060471-B2
    优先权日:2003-03-12
    标题 :Stereoselective chemoenzymatic process for the preparation of optically enriched phenylglycidates as precursors of taxol side chain
    发明人:ANAND NAVEEN; KAPOOR MUNISH; TANEJA SUBHASH CHANDRA; KOUL SURRINDER; SHARMA RATTAN LAL; QAZI GHULAM NABI
    权利人:COUNCIL SCIENT IND RES
    摘要:The present invention relates to a novel and efficient chemoenzymatic process of preparation of optically active trans alkyl phenylglycidates. The invention particularly discloses a novel process for the chemoenzymatic synthesis of two enantiomers of trans alkyl phenylglycidate i.e. alkyl(2S,3R)-phenylglycidate and alkyl(2R,3S)-phenylglycidate of formulae 7 and 8 respectively

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    ✅ COA系统入驻 | 共享模式

    主要参考文献

    [参考文献]: Iwao Ojima, Et Al. Efficient And Practical Asymmetric Synthesis Of The Taxol C-13 Side Chain, N-Benzoyl-(2R,3S)-3-Phenylisoserinea,N D Its Analogues Via Chiral3-Hydroxy-4-Aryl-&lactams Through Chiral Ester Enolate-Imine Cyclocondensation.
    [参考文献]: E K Rowinsky, Et Al. Sequences Of Taxol And Cisplatin: A Phase I And Pharmacologic Study. J Clin Oncol. 1991 Sep;9(9):1692-703.

    合成参考文献


    摘要:Duschmalé, J.; Arakawa, Y.; Wennemers, H., Science of Synthesis: Asymmetric Organocatalysis, (2012) 2, 741.
    参考文献:10.1021/np0304565
    摘要:Tremblay S, Soucy C, Towers N, Gunning PJ, Breau L. Characterization of an abeo-Taxane: Brevifoliol and Derivatives. J. Nat. Prod. 2004 Apr 27;67(5):838–45. doi: 10.1021/np0304565.
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