CAS: 92051-23-5; (2S,3S,4S,5R,6R)-6-(Acetoxymethyl)-3-(((Trifluoromethyl)Sulfonyl)Oxy)Tetrahydro-2H-Pyran-2,4,5-Triyl Triacetate

该化合物是六碳甘蔗的衍生物,这种化合物具有多种乙酰组和三氟酸盐组,可增强其在有机溶剂中的回活性和溶性.乙酰组的存在表明,糖上的氢氧基组是乙基酸,通常能改善稳定性并改变化合物的物理特性.三氟酸三甲酯组是一个强大的离子组,使这种化合物在有机合成中特别有用,特别是在玻璃相合反应中.亚丙烯酸组的配置表明,亚丙酰基化合物处于赤道位置,影响化合物的立体化学化学和再活性.这种化合物经常用于碳氢化化学,以合成更为复杂的寡烯酸亚酸和胶表面.它独特的结构特征使它在生物技术和生物化学化合物的开发过程中成为宝贵的中间体.

结构式图片

上下游产品

trifluoromethylsulfonic anhydride 1,3,4,6-tetra-O-acetyl-β-D-mannopyranose D-Mannose pentaacetate 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside

合成工艺路线路线简述

  • 18968-05-3 + 358-23-6 = 92051-23-5
    反应条件:1.1 Reagents: Pyridine Solvents: Dichloromethane; Rt
    标题:A Solid-Phase Route To 18F-Labeled Tracers,Exemplified By The Synthesis Of [18F]2-Fluoro-2-Deoxy-D-Glucose
    作者:Brown,Lynda J.; Bouvet,Denis R.; Champion,Sue; Gibson,Alex M.; Hu,Yulai; Et Al
    参考文献:Angewandte Chemie 日期:2007 卷标:46(6) 页码:941-944]

    18968-05-3 + 358-23-6 = 92051-23-5
    反应条件:1.1 Reagents: Triethylamine Solvents: Dichloromethane; Rt -> -15 °C1.2 -20 - -15 °C; 30 Min,-20 - -15 °C; -15 °C -> Rt
    标题:An Improved Synthesis Of 1,3,4,6-Tetra-O-Acetyl-2-O-Trifluoromethane Sulfonyl-β-D-Mannopyranose
    作者:Li,You; Cao,Yucai
    参考文献:Jingxi Huagong 日期:2009 卷标:26(6) 页码:620-624]

    18968-05-3 + 358-23-6 = 92051-23-5 [标题:Reaction Conditions
    标题:1,3,4,6-Tetra-O-Acetyl-2-(Trifluoromethylsulfonyl)-β-D-Mannopyranose
    作者:Zhu,Hong Yuan; Jiang,Shen De
    参考文献:Acta Crystallographica 日期:2007 卷标:63(6)]

    18968-05-3 + 358-23-6 = 92051-23-5
    反应条件:1.1 Solvents: Dichloromethane,Pyridine
    标题:Reactions Of Per-O-Acetylated Carbohydrate Triflates With Halide Ions
    作者:Binkley,Roger W.; Ambrose,Michael G.; Hehemann,David G.
    参考文献:Journal Of Carbohydrate Chemistry 日期:1987 卷标:6(2) 页码:203-19]

    = 92051-23-5 [标题:Reaction Conditions
    标题:Method Of Synthesis Of [2-18F]-2-Deoxyglucose
    参考文献:Russian Federation]

    = 92051-23-5 [标题:Reaction Conditions
    标题:Stereoselective Solid-Phase Glycosidation Of Sulfinyl Hexoses In Preparation Of Disaccharides
    参考文献:World Intellectual Property Organization]

    18968-05-3 + 358-23-6 = 92051-23-5
    反应条件:1.1 Reagents: Pyridine Solvents: Dichloromethane; Rt -> -20 °C; 1 H,-20 °C; 1 H,Rt
    标题:A Biosynthetic Pathway For Be-7585A,A 2-Thiosugar-Containing Angucycline-Type Natural Product
    作者:Sasaki,Eita; Ogasawara,Yasushi; Liu,Hung-Wen
    参考文献:Journal Of The American Chemical Society 日期:2010 卷标:132(21) 页码:7405-7417]

    18968-05-3 + 358-23-6 = 92051-23-5
    反应条件:1.1 Reagents: Pyridine Solvents: Dichloromethane; -15 °C; -15 °C -> Rt
    标题:Synthesis Of The Positron-Emitting Radiotracer [18F]-2-Fluoro-2-Deoxy-D-Glucose From Resin-Bound Perfluoroalkylsulfonates
    作者:Brown,Lynda J.; Ma,Nianchun; Bouvet,Denis R.; Champion,Sue; Gibson,Alex M.; Et Al
    参考文献:Organic & Biomolecular Chemistry 日期:2009 卷标:7(3) 页码:564-575]

    18968-05-3 + 358-23-6 = 92051-23-5
    反应条件:1.1 Reagents: Pyridine Solvents: Dichloromethane1.2 -
    标题:Synthesis Of Ligands Related To The O-Specific Antigen Of Shigella Dysenteriae Type 1. Part 1. A Short Synthesis Of 1,3,4,6-Tetra-O-Acetyl-2-Azido-2-Deoxy-β-D-Glucopyranose And The Corresponding α-Glucosyl Chloride From D-Mannose
    作者:Pavliak,Viliam; Kovac,Pavol
    参考文献:Carbohydrate Research 日期:1991 卷标:210 页码:333-7]

    18968-05-3 + 358-23-6 = 92051-23-5
    反应条件:1.1 Reagents: Pyridine Solvents: Acetonitrile; Cooled; 2 H,25 °C
    标题:Method For Producing 2-Deoxy-2-Fluoroglucose
    参考文献:Japan]

    18968-05-3 + 358-23-6 = 92051-23-5
    反应条件:1.1 Reagents: Pyridine Solvents: Acetonitrile; Cooled; 2 H,25 °C
    标题:Production Method For 2-Deoxy-2-Fluoroglucose
    参考文献:World Intellectual Property Organization]

    18968-05-3 + 358-23-6 = 92051-23-5
    反应条件:1.1 Reagents: Pyridine Solvents: Dichloromethane; 40 Min,-15 °C; 6 H,Rt
    标题:Modified Method For Preparing 1,3,4,6-Tetraacetyl-β-D-Mannopyranose As Intermediate Of Mannose Triflate
    参考文献:China]

    18968-05-3 + 358-23-6 = 92051-23-5
    反应条件:1.1 Reagents: Pyridine Solvents: Dichloromethane; Rt -> -15 °C1.2 25 Min,-15 °C; Overnight,-15 °C -> Rt
    标题:Synthesis,Photophysical Properties,And Photodynamic Activity Of Positional Isomers Of Tfpp-Glucose Conjugates
    作者:Fadlan,Arif; Tanimoto,Hiroki; Ito,Tatsuya; Aritomi,Yusuke; Ueno,Maho; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2018 卷标:26(8) 页码:1848-1858]

    18968-05-3 + 358-23-6 = 92051-23-5
    反应条件:1.1 Reagents: Pyridine Solvents: Dichloromethane; -20 °C
    标题:Preparation Of Mercaptodeoxyglucose-Gold Complexes As Anticancer Agents
    参考文献:World Intellectual Property Organization]

    18968-05-3 + 1493-13-6 = 92051-23-5
    反应条件:1.1 Solvents: Dichloromethane,Pyridine; 45 Min,-25 °C
    标题:Preparation Method Of Trifluoromannose
    参考文献:China]

    18968-05-3 + 1493-13-6 = 92051-23-5
    反应条件:1.1 Catalysts: Pyridine,1-Butyl-3-Methylimidazolium Trifluoromethanesulfonate Solvents: Dichloromethane; Rt -> -25 °C1.2 45 Min,-25 °C
    标题:Preparation Of 1,3,4,6-Tetraacetyl-2-O-Trifluromethanesulfonyl-β-D-Mannopyranose As Intermediate For 18F-Labeled Positron Radioactive Tracer
    参考文献:China]

    = 92051-23-5 [标题:Reaction Conditions
    标题:Method And Device For Synthesizing Labeled Sugars
    参考文献:World Intellectual Property Organization]

    = 92051-23-5 [标题:Reaction Conditions
    标题:Preparation Of Antitumor Oligosaccharide-Based Ligands Combinatorial Library Via Solid-Support Glycosidation Reaction
    参考文献:World Intellectual Property Organization]

    = 92051-23-5 [标题:Reaction Conditions
    标题:A Convenient Synthesis For Anomeric 2-Thioglucobioses,2-Thiokojibiose And 2-Thiosophorose
    作者:Defaye,Jacques; Guillot,Jean Michel
    参考文献:Carbohydrate Research 日期:1994 卷标:253 页码:185-94]

    = 92051-23-5 [标题:Reaction Conditions
    标题:Synthesis Of Fluorine-18-Labeled 2-Deoxy-2[18F]Fluoro-D-Glucose And Its Precursors For Human Diagnostics
    作者:Toth,Gyula; Mikecz,Pal; Molnar,Tamas; Tron,Lajos
    参考文献:Izotoptechnika 日期:1992 卷标:35(2) 页码:65-72
1,3,4,6-四-氧-乙酰-β-D-吡啶甘露糖置于吡啶,Trifluoromethanesulfonic Acid Anhydride体系中,用 二氯甲烷 作为反应溶剂,以1.59 G (77%)的收率获得产物甘露糖三氟磺酸酯
参考文献:Sulfinyl Hexose Derivatives Useful For Glycosylation
标题:Sulfinyl Hexose Derivatives Useful For Glycosylation
摘要:描述了一种帮助控制固相糖基化反应过程中形成的糖苷键立体化学的己糖衍生物.还描述了它们的使用方法.

海关参考信息

专利信息


专利号:US-7829032-B2
优先权日:2007-01-23
标题 :Fully-automated microfluidic system for the synthesis of radiolabeled biomarkers for positron emission tomography
发明人:VAN DAM ROBERT MICHAEL; BALL CARROLL EDWARD; ELIZAROV ARKADIJ M; KOLB HARTMUTH C
权利人:SIEMENS MEDICAL SOLUTIONS
摘要:The present application relates to microfluidic devices and related technologies, and to chemical processes using such devices. More specifically, the application discloses a fully automated synthesis of radioactive compounds for imaging, such as by positron emission tomography (PET), in a fast, efficient and compact manner. In particular, this application describe an automated, stand-alone, microfluidic instrument for the multi-step chemical synthesis of radiopharmaceuticals, such as probes for PET and a method of using such instruments.

专利号:US-8333952-B2
优先权日:2009-09-23
标 题:Dose synthesis module for biomarker generator system
发明人:NUTT RONALD; GIAMIS ANTHONY M; MCFARLAND AARON
权利人:NUTT RONALD; GIAMIS ANTHONY M; MCFARLAND AARON; ABT MOLECULAR IMAGING INC
摘要:A microfluidic radiopharmaceutical production system and process for synthesizing per run approximately, but not less than, one (1) unit dose of a radiopharmaceutical biomarker for use in positron emission tomography (PET). The radiopharmaceutical production system includes a reaction vessel that receives a radioisotope from an accelerator or other radioisotope generator. Organic and aqueous reagents are introduced into the reaction vessel, and the mixture is heated to synthesize a solution of a pre-selected radiopharmaceutical. The radiopharmaceutical solution is purified by passing the solution through a solid phase extraction column and a filter. The synthesis process produces per run a quantity of radiopharmaceutical approximately equal to, but not less than, one (1) unit dose of a radiopharmaceutical, reducing waste and allowing for the production of radiopharmaceutical on an as-needed basis. The synthesis process allows for the production of biomarker radiopharmaceuticals on site and close to the location where the unit dose will be administered to the patient. On-site, as-needed production of radiopharmaceuticals in small doses reduces the time between the synthesis of the radiopharmaceutical and the administration of that radiopharmaceutical, thereby minimizing the loss of active isotopes through decay and allowing the production of lesser amounts of radioisotopes overall.

专利号:US-10109385-B2
优先权日:2009-09-23
标题:Dose synthesis card for use with automated biomarker production system
发明人:MCFARLAND AARON; ANZELLOTTI ATILIO; HILLESHEIM DANIEL; BROWN-PROCTOR CLIVE; KHACHATURIAN MARK HAIG; LAND ANDREW
权利人:ABT MOLECULAR IMAGING INC
摘要:Microfluidic radiopharmaceutical production system and process for synthesizing per run approximately, but not less than, ten (10) unit doses of radiopharmaceutical biomarker for use in positron emission tomography (PET). A radioisotope from an accelerator or other radioisotope generator is introduced into a reaction vessel, along with organic and aqueous reagents, and the mixture heated to synthesize a solution of a pre-selected radiopharmaceutical. The solution is purified by passing through a combination of solid phase extraction purification components, trap and release components, and a filter. The synthesis process reduces waste and allows for production of biomarker radiopharmaceuticals on site and close to the location where the unit dose will be administered to the patient. On-site, as-needed production of radiopharmaceuticals in small doses reduces the time between synthesis of the radiopharmaceutical and administration of that radiopharmaceutical, minimizing loss of active isotopes through decay and allowing production of lesser amounts of radioisotopes overall.

专利号:US-8273300-B2
优先权日:2009-07-09
标题 :Modular system for radiosynthesis with multi-run capabilities and reduced risk of radiation exposure
发明人:ELIZAROV ARKADIJ M; BALL CARROLL EDWARD; ZHANG JIANZHONG; KOLB HARTMUTH C; MIRAGHAIE REZA; GRAVES TODD; LEBEDEV ARTEM
权利人:ELIZAROV ARKADIJ M; BALL CARROLL EDWARD; ZHANG JIANZHONG; KOLB HARTMUTH C; MIRAGHAIE REZA; GRAVES TODD; LEBEDEV ARTEM; SIEMENS MEDICAL SOLUTIONS
摘要:Macro- and microfluidic devices and related technologies, and chemical processes using such devices. More specifically, the devices may be used for a fully automated synthesis of radioactive compounds for imaging, such as by positron emission tomography (PET), in an efficient, compact and safe to the operator manner. In particular, embodiments of the present invention relate to an automated, multi-run, microfluidic instrument for the multi-step synthesis of radiopharmaceuticals, such as PET probes, comprising a remote shielded mini-cell containing radiation-handing components.

专利号:US-8435454-B2
优先权日:2009-07-09
标 题:Modular system for radiosynthesis with multi-run capabilities and reduced risk of radiation exposure
发明人:ELIZAROV ARKADIJ M; BALL CARROLL EDWARD; ZHANG JIANZHONG; KOLB HARTMUTH C; MIRAGHAIE REZA; GRAVES TODD L; LEBEDEV ARTEM; SCHLEIFFER KEITH E
权利人:ELIZAROV ARKADIJ M; BALL CARROLL EDWARD; ZHANG JIANZHONG; KOLB HARTMUTH C; MIRAGHAIE REZA; GRAVES TODD L; LEBEDEV ARTEM; SCHLEIFFER KEITH E; SIEMENS MEDICAL SOLUTIONS
摘要:Macro- and microfluidic devices and related technologies, and chemical processes using such devices. More specifically, the devices may be used for a fully automated synthesis of radioactive compounds for imaging, such as by positron emission tomography (PET), in an efficient, compact and safe to the operator manner. In particular, embodiments of the present invention relate to an automated, multi-run, microfluidic instrument for the multi-step synthesis of radiopharmaceuticals, such as PET probes, comprising a remote shielded mini-cell containing radiation-handing components.

专利号:US-7714115-B2
优先权日:2004-10-05
标 题 :Method of deprotection
发明人:GRIGG JULIAN; OSBORN NIGEL
权利人:GE HEALTHCARE LTD
摘要:The invention provides a method for the synthesis of an 18F-labelled product comprising deprotected of a protected 18F-labelled compound using a deprotection agent comprising a weak acid and wherein neutralisation and buffering of the deprotected product are carried out by the addition of a neutralisation agent. The deprotected product is buffered in a pH range suitable for subsequent autoclaving and formulation into an injectable radiopharmaceutical.
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主要参考文献

参考标题:Azide And Cyanide Displacements Via Hypervalent Silicate Intermediates
作者:Eric D. Soli,Amy S. Manoso,Michael C. Patterson,Philip Deshong,David A. Favor,Ralph Hirschmann,Amos B. Smith |发布日期:1999.4.1
摘要:Respectively, With Tetrabutylammonium Fluoride, Are Effective Sources Of Nucleophilic Azide Or Cyanide. Primary And Secondary Alkyl Halides And Sulfonates Undergo Rapid And Efficient Azide Or Cyanide Displacement In The Absence Of Phase Transfer Catalysts With The Silicate Derivatives. Application Of These Reagents To The Stereoselective Synthesis Of Glycosyl Azide Derivatives Is Reported.

合成参考文献


参考文献:10.1007/s11307-011-0504-4
摘要:Keen H, Pichler B, Kukuk D, Duchamp O, Raguin O, Shannon A, Whalley N, Jacobs V, Bales J, Gingles N, Ricketts SA, Wedge SR. An evaluation of 2-deoxy-2-[18F]fluoro-D-glucose and 3'-deoxy-3'-[18F]-fluorothymidine uptake in human tumor xenograft models. Mol Imaging Biol. 2012 Jun;14(3):355–65. doi: 10.1007/s11307-011-0504-4.
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