一种蛋白酶抑制剂二肽类似物的不对称二羟基化合成路线：利托那韦核心单元的对映选择性合成。
Asymmetric dihydroxylation route to a dipeptide isostere of a protease inhibitor: enantioselective synthesis of the core unit of ritonavir.
作者信息
Ghosh Arun K, Shin Dongwoo, Mathivanan Packiarajan
机构信息
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, USA.,
出版信息
Chem Commun (Camb). 1999;1999(11):1025-1026. doi: 10.1039/A902518I.
Abstract
An enantioselective synthesis of the dipeptide isostere of ritonavir has been accomplished utilizing Sharpless asymmetric hydroxylation as the key step.
摘要
利用夏普莱斯不对称羟基化作为关键步骤，已完成了利托那韦二肽类似物的对映选择性合成。
相似文献
1
Asymmetric dihydroxylation route to a dipeptide isostere of a protease inhibitor: enantioselective synthesis of the core unit of ritonavir.一种蛋白酶抑制剂二肽类似物的不对称二羟基化合成路线：利托那韦核心单元的对映选择性合成。
Chem Commun (Camb). 1999;1999(11):1025-1026. doi: 10.1039/A902518I.
2
Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review.Sharpless 不对称双羟化反应：天然产物合成的杰出工具——综述
Molecules. 2023 Mar 17;28(6):2722. doi: 10.3390/molecules28062722.
3
De novo asymmetric syntheses of D- and L-talose via an iterative dihydroxylation of dienoates.通过二烯酸酯的迭代双羟基化反应对D-和L-塔罗糖进行从头不对称合成。
J Org Chem. 2005 Dec 9;70(25):10576-8. doi: 10.1021/jo051476+.
4
De novo asymmetric syntheses of muricatacin and its analogues via dihydroxylation of dienoates.通过二烯酸酯的二羟基化反应从头不对称合成多节孢菌素及其类似物。
J Org Chem. 2006 Aug 18;71(17):6686-9. doi: 10.1021/jo061057s.
5
De novo asymmetric syntheses of C-4-substituted sugars via an iterative dihydroxylation strategy.通过迭代二羟基化策略进行C-4-取代糖的从头不对称合成。
Carbohydr Res. 2006 Jul 24;341(10):1505-21. doi: 10.1016/j.carres.2006.03.024. Epub 2006 Apr 17.
6
Enantioselective synthesis of pachastrissamine (jaspin B) using dirhodium(II)-catalyzed C-H amination and asymmetric dihydroxylation as key steps.以二铑（II）催化的C-H胺化反应和不对称二羟基化反应为关键步骤，对帕卡司他明（jaspi B）进行对映选择性合成。
Chem Pharm Bull (Tokyo). 2007 Aug;55(8):1284-6. doi: 10.1248/cpb.55.1284.
7
Short, Divergent, and Enantioselective Total Synthesis of Bioactive -Pimaranes.短链、发散、对映选择性全合成生物活性 -Pimaranes。
Org Lett. 2022 Oct 7;24(39):7151-7156. doi: 10.1021/acs.orglett.2c02843. Epub 2022 Sep 28.
8
An efficient, stereoselective synthesis of the hydroxyethylene dipeptide isostere core for the HIV protease inhibitor A-792611.用于HIV蛋白酶抑制剂A-792611的高效、立体选择性合成羟乙烯二肽等排体核心。
J Org Chem. 2006 Jul 7;71(14):5369-72. doi: 10.1021/jo060737s.
9
An electrophilic cleavage procedure for the asymmetric dihydroxylation: direct enantioselective synthesis of cyclic boronic esters from olefins.一种用于不对称二羟基化的亲电裂解方法：由烯烃直接对映选择性合成环状硼酸酯。
Chemistry. 2005 Jun 20;11(13):3951-8. doi: 10.1002/chem.200500095.
10
Enantioselective synthesis of 10-epi-anamarine via an iterative dihydroxylation sequence.通过迭代双羟基化序列对10-表阿那马林进行对映选择性合成。
Org Lett. 2005 Mar 17;7(6):1069-72. doi: 10.1021/ol047322i.
引用本文的文献
1
An enantioselective synthesis of the C-C segment of antitumor macrolide peloruside A.抗肿瘤大环内酯类化合物peloruside A碳-碳片段的对映选择性合成。
Tetrahedron Lett. 2003 May 12;44(20):3967-3969. doi: 10.1016/S0040-4039(03)00744-5. Epub 2003 Apr 24.
2
Syntheses of FDA Approved HIV Protease Inhibitors.美国食品药品监督管理局批准的HIV蛋白酶抑制剂的合成
Synthesis (Stuttg). 2001;2001(15):2203-2229. doi: 10.1055/s-2001-18434.
本文引用的文献
1
STEREOCONTROLLED SYNTHESIS OF HIV-l PROTEASE INHIBITORS WITH C-AXIS OF SYMMETRY.具有C对称轴的HIV-1蛋白酶抑制剂的立体控制合成。
Tetrahedron Lett. 1991 Oct 7;32(41):5729-5732. doi: 10.1016/S0040-4039(00)93541-X. Epub 2001 Mar 26.
2
Potent HIV-1 Protease Inhibitors: Stereoselective Synthesis of a Dipeptide Mimic.强效HIV-1蛋白酶抑制剂：二肽模拟物的立体选择性合成
J Org Chem. 1993 Feb;58(5):1025-1029. doi: 10.1021/jo00057a011.
3
Transition-State Mimetics for HIV Protease Inhibitors: Stereocontrolled Synthesis of Hydroxyethylene and Hydroxyethylamine Isosteres by Ester-Derived Titanium Enolate Syn and Anti-Aldol Reactions.用于HIV蛋白酶抑制剂的过渡态模拟物：通过酯衍生的钛烯醇盐顺式和反式羟醛缩合反应立体控制合成羟乙烯和羟乙胺电子等排体
J Org Chem. 1998 Sep 4;63(18):6146-6152. doi: 10.1021/jo980159i.
4
Total Synthesis of (+)-Sinefungin.
J Org Chem. 1996 Sep 6;61(18):6175-6182. doi: 10.1021/jo960670g.
5
A 24-week open-label phase I/II evaluation of the HIV protease inhibitor MK-639 (indinavir).HIV蛋白酶抑制剂MK-639（茚地那韦）的一项为期24周的开放标签I/II期评估。
AIDS. 1996 May;10(5):485-92. doi: 10.1097/00002030-199605000-00006.
6
The effect of high-dose saquinavir on viral load and CD4+ T-cell counts in HIV-infected patients.高剂量沙奎那韦对HIV感染患者病毒载量和CD4 + T细胞计数的影响。
Ann Intern Med. 1996 Jun 15;124(12):1039-50. doi: 10.7326/0003-4819-124-12-199606150-00003.
7
HIV protease as an inhibitor target for the treatment of AIDS.HIV蛋白酶作为治疗艾滋病的抑制剂靶点。
Adv Pharmacol. 1994;25:399-454. doi: 10.1016/s1054-3589(08)60438-x.
8
L-735,524: an orally bioavailable human immunodeficiency virus type 1 protease inhibitor.
Proc Natl Acad Sci U S A. 1994 Apr 26;91(9):4096-100. doi: 10.1073/pnas.91.9.4096.
9
ABT-538 is a potent inhibitor of human immunodeficiency virus protease and has high oral bioavailability in humans.ABT-538是一种强效的人类免疫缺陷病毒蛋白酶抑制剂，在人体中具有高口服生物利用度。
Proc Natl Acad Sci U S A. 1995 Mar 28;92(7):2484-8. doi: 10.1073/pnas.92.7.2484.
10
Diphenylphosphoryl azide. A new convenient reagent for a modified Curtus reaction and for the peptide synthesis.二苯基磷酰叠氮化物。一种用于改良库尔提斯反应和肽合成的新型便捷试剂。
J Am Chem Soc. 1972 Aug 23;94(17):6203-5. doi: 10.1021/ja00772a052.
Zotero 插件