CAS: 80040-79-5; Tri-O-Benzyl-D-Galactal

该化合物是一种化学化合物,其特点是附于星际结构的三个苯基组,它是伽丽菊酯的衍生物;这种化合物通常用于有机合成和碳水化合物化学,因为它能够作为甘基基酰捐献者或接受者,或各种反应中的接受者;一种白色的非白色固体,溶于二氯甲烷和乙基乙酸等有机溶剂,但一般在水中无法溶解; 苯基组的存在加强了其稳定性和再活性,使其在更复杂的碳水化合物结构合成中有用; 此外,三-O苯并苯-D-藻类可以进行各种化学转化,包括脱氧和同温反应,这些反应对于发展藻类表面和亚基亚酸盐类,至关重要;其分子结构和特性使其成为医药化学和生物活性化合物合成领域的宝贵中间体.

英文名称Tri-O-Benzyl-D-Galactal
中文名称三-O-苄基-D-半乳醛
IUPAC名称(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran
其它别名(2R,3R,4R)-3,4-Bis(Benzyloxy)-2-((Benzyloxy)Methyl)-3,4-Dihydro-2H-Pyran; Tri-O-Benzyl-D-Galactal, ; 3,4,6-Tri-O-Benzyl-D-Galactal; 1,5-Anhydro-2-Deoxy-D-Lyxo-Hex-1-Enitol 3,4,6-
CAS编号80040-79-5
MFCD编号:MFCD09039276
分子式:C27H28O4
分子量:416.51
产品CID: 1794420
产品分类生物化工 → 糖类化合物 → 单糖

相似结构搜索
InChIKey: MXYLLYBWXIUMIT-ZONZVBGPSA-N
InChI=1/C27H28O4/c1-4-10-22(11-5-1)18-28-21-26-27(31-20-24-14-8-3-9-15-24)25(16-17-29-26)30-19-23-12-6-2-7-13-23/h1-17,25-27H,18-21H2/t25-,2…
计算化学: 氢键受体数4.0氢键供体数0.0可旋转键数10.0

物理性质

熔点57-58 °C(文献)
沸点544.9 °C at 760 mmHg
闪点129.7 °C
密度1.16 g/cm3
PSA:36.92
LogP:5.2865
折射率-34 ° (C=1, MeOH)
蒸汽压2.24E-11 mmHg at 25 °C
溶解性Soluble In Dichloromethane Or Chloroform,
敏感性常温常压下稳定，远离氧化剂。
外观形态白色至黄色粉末
储存条件密封干燥,冷冻保存, 低于 -20°C
产品应用该化合物用于该化合物用于静脉选择性合成物.

上下游产品

合成工艺路线路线简述

21193-75-9 = 80040-79-5
反应条件:1.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran; 30 Min,Rt; 0 °C1.2 5 Min,0 °C; 10 Min,0 °C; Overnight1.3 Reagents: Methanol; Rt
标题:A Concise Synthesis Of N-Substituted Fagomine Derivatives And The Systematic Exploration Of Their α-Glycosidase Inhibition
作者:Jiang,Fu-Xiang; Liu,Qiao-Zhen; Zhao,Dan; Luo,Cui-Ting; Guo,Cui-Ping; Et Al
参考文献:European Journal Of Medicinal Chemistry 日期:2014 卷标:77 页码:211-222]

4098-06-0 = 80040-79-5
反应条件:1.1 Reagents: Sodium Hydroxide Catalysts: Tetrabutylammonium Iodide Solvents: Tetrahydrofuran; 3 H,Rt
标题:Direct One-Pot Conversion Of Acylated Carbohydrates Into Their Alkylated Derivatives Under Heterogeneous Reaction Conditions Using Solid Naoh And A Phase Transfer Catalyst
作者:Madhusudan,Soni Kamlesh; Agnihotri,Geetanjali; Negi,Devendra S.; Misra,Anup Kumar
参考文献:Carbohydrate Research 日期:2005 卷标:340(7) 页码:1373-1377]

21193-75-9 = 80040-79-5
反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide; 0 °C1.2 -
标题:Immunomodulatory α-Galactoglycosphingolipids: Synthesis Of 2'-Fluoro-2'-Deoxy-α-Galactosylceramide And An Evaluation Of Its Immunostimulating Properties
作者:Barbieri,Lucia; Costantino,Valeria; Fattorusso,Ernesto; Mangoni,Alfonso; Basilico,Nicoletta; Et Al
参考文献:European Journal Of Organic Chemistry 日期:2005 卷标:(15) 页码:3279-3285]

21193-75-9 = 80040-79-5
反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide; 0 °C1.2 0 °C; 12 H,Rt
标题:Immunomodulatory α-Galactoglycosphingolipids: Synthesis Of A 2'-O-Methyl-α-Gal-Gsl And Evaluation Of Its Immunostimulating Capacity
作者:Barbieri,Lucia; Costantino,Valeria; Fattorusso,Ernesto; Mangoni,Alfonso; Aru,Elisabetta; Et Al
参考文献:European Journal Of Organic Chemistry 日期:2004 卷标:(3) 页码:468-473]

21193-75-9 = 80040-79-5
反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide; 30 Min,0 °C1.2 16 H,Rt1.3 Reagents: Methanol; Rt
标题:α-Selective Glycosylation With β-Glycosyl Sulfonium Ions Prepared Via Intramolecular Alkylation
作者:Moons,Sam J.; Mensink,Rens A.; Bruekers,Jeroen P. J.; Vercammen,Maurits L. A.; Jansen,Laura M.; Et Al
参考文献:Journal Of Organic Chemistry 日期:2019 卷标:84(7) 页码:4486-4500]

4098-06-0 = 80040-79-5
反应条件:1.1 Reagents: Sodium Methoxide Solvents: Methanol; 4 H,0 °C1.2 Reagents: Sodium Hydride Solvents: Dimethylformamide; 0 °C; 30 Min,0 °C1.3 0 °C; 12 H,0 °C1.4 Reagents: Ammonium Chloride Solvents: Water
标题:Rhodium-Catalyzed Denitrogenative Trans-Annulation Of N-Sulfonyl-1,2,3-Triazoles With Glycals Giving Pyrroline-Fused N-Glycosides
作者:Bi,Jingjing; Tan,Qiang; Wu,Hao; Liu,Qingfeng; Zhang,Guisheng
参考文献:Organic Letters 日期:2021 卷标:23(16) 页码:6357-6361]

4098-06-0 = 80040-79-5
反应条件:1.1 Reagents: Sodium Methoxide; 0 °C; 1 H,Rt1.2 Reagents: Amberlite Ir 120; Neutralized1.3 Reagents: Sodium Hydride Solvents: Dimethylformamide; 40 Min,0 °C1.4 0 °C -> Rt; 16 H,Rt1.5 Reagents: Methanol; 15 Min
标题:Fluorine-Directed β-Galactosylation: Chemical Glycosylation Development By Molecular Editing
作者:Durantie,Estelle; Bucher,Christoph; Gilmour,Ryan
参考文献:Chemistry - A European Journal 日期:2012 卷标:18(26) 页码:8208-8215]

21193-75-9 = 80040-79-5
反应条件:1.1 Reagents: Sodium Hydride
标题:Glycal-Mediated Synthesis Of Enantiomerically Pure 5-Substituted Isoxazoles Containing A Differentially O-Benzylated Glycerol Moiety
作者:Weinig,Hans-Georg; Passacantilli,Pietro; Colapietro,Marcello; Piancatelli,Giovanni
参考文献:Tetrahedron Letters 日期:2002 卷标:43(26) 页码:4613-4615]

21193-75-9 = 80040-79-5
反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide; 0 °C; 30 Min,0 °C -> Rt
标题:Glycomimetic Ligands For The Human Asialoglycoprotein Receptor
作者:Mamidyala,Sreeman K.; Dutta,Sanjay; Chrunyk,Boris A.; Preville,Cathy; Wang,Hong; Et Al
参考文献:Journal Of The American Chemical Society 日期:2012 卷标:134(4) 页码:1978-1981]

21193-75-9 = 80040-79-5
反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide; 15 Min,0 °C1.2 16 H,Rt1.3 Reagents: Methanol; Rt
标题:C-2 Auxiliaries For Stereoselective Glycosylation Based On Common Additive Functional Groups
作者:De Kleijne,Frank F. J.; Moons,Sam J.; White,Paul B.; Boltje,Thomas J.
参考文献:Organic & Biomolecular Chemistry 日期:2020 卷标:18(6) 页码:1165-1184]

21193-75-9 = 80040-79-5
反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide; 45 Min,Rt; Rt -> 0 °C1.2 0 °C; 12 H,Rt; Rt -> 0 °C1.3 Reagents: Methanol; 0 °C
标题:Total Synthesis Of The Congested,Bisphosphorylated Morganella Morganii Zwitterionic Trisaccharide Repeating Unit
作者:Keith,D. Jamin; Townsend,Steven D.
参考文献:Journal Of The American Chemical Society 日期:2019 卷标:141(32) 页码:12939-12945]

21193-75-9 = 80040-79-5
反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide,Tetrahydrofuran; 0 °C; 4 H,60 °C; Cooled1.2 Reagents: Carbon Dioxide Solvents: Diethyl Ether,Water; Neutralized,Rt
标题:Stereoselective Michael-Type Addition Of Organocopper Reagents To Enones Derived From Glycals In The Synthesis Of 2-Phosphono-α-C-Glycosides
作者:Leonelli,Francesca; Capuzzi,Marinella; Calcagno,Vincenzo; Passacantilli,Pietro; Piancatelli,Giovanni
参考文献:European Journal Of Organic Chemistry 日期:2005 卷标:(13) 页码:2671-2676]

4098-06-0 = 80040-79-5
反应条件:1.1 Reagents: Sodium Methoxide Solvents: Methanol; 3 H,0 °C1.2 Reagents: Sodium Hydride Solvents: Dimethylformamide; 0 °C; 20 Min,0 °C1.3 0 °C; 12 H,0 °C1.4 Reagents: Ammonium Chloride Solvents: Water
标题:Direct C-H Trifluoromethylation Of Glycals By Photoredox Catalysis
作者:Wang,Bang; Xiong,De-Cai; Ye,Xin-Shan
参考文献:Organic Letters 日期:2015 卷标:17(22) 页码:5698-5701]

= 80040-79-5
反应条件:1.1 Reagents: Sodium Acetate Solvents: Tetrahydrofuran; Rt -> 0 °C1.2 Reagents: Copper,Zinc; 4.5 H,0 °C -> 10 °C
标题:General Method For Synthesizing Pyranoid Glycals. A New Route To Allal And Gulal Derivatives
作者:Boutureira,Omar; Rodriguez,Miguel Angel; Matheu,M. Isabel; Diaz,Yolanda; Castillon,Sergio
参考文献:Organic Letters 日期:2006 卷标:8(4) 页码:673-675]

4098-06-0 = 80040-79-5
反应条件:1.1 Reagents: Sodium Methoxide Solvents: Methanol; 1 H,0 °C -> Rt1.2 Reagents: Sodium Hydride Solvents: Dimethylformamide; 30 Min,0 °C; 30 Min,0 °C1.3 0 °C; Overnight,Rt1.4 Reagents: Water
标题:Reengineering Chemical Glycosylation: Direct,Metal-Free Anomeric O-Arylation Of Unactivated Carbohydrates
作者:Lucchetti,Nicola; Gilmour,Ryan
参考文献:Chemistry - A European Journal 日期:2018 卷标:24(61) 页码:16266-16270]

4098-06-0 = 80040-79-5
反应条件:1.1 Reagents: Sodium Methoxide Solvents: Methanol; 2 H,Rt1.2 Reagents: Carbon Dioxide; Neutralized,Rt1.3 Reagents: Sodium Hydride Solvents: Dimethylformamide; 0 °C; 16 H,0 °C -> Rt
标题:α-Glycosphingolipids Via Chelation-Induced Anomerization Of O- And S-Glucuronic And Galacturonic Acid Derivatives
作者:Pilgrim,Wayne; Murphy,Paul V.
参考文献:Organic Letters 日期:2009 卷标:11(4) 页码:939-942]

21193-75-9 = 80040-79-5
反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Dimethyl Sulfoxide; 1 D,Rt1.2 Reagents: Sodium Hydroxide Solvents: Dimethyl Sulfoxide; 6 D,Rt1.3 Reagents: Water; Rt
标题:Bronsted Acid-Catalyzed Ring-Opening Polycondensation Of Galactose-Based Cyclic Sulfite
作者:Miyazaki,Ryo; Suzuki,Misaki; Shetty,Sangeetha Srinivasa; Shimazaki,Taichi; Osaka,Issey; Et Al
参考文献:Polymer Journal (Tokyo 日期:2023 卷标:55(3) 页码:213-221]

4098-06-0 = 80040-79-5
反应条件:1.1 Catalysts: Potassium Carbonate Solvents: Methanol; 3 H,Rt1.2 Reagents: Sodium Hydride Solvents: Dimethylformamide; 0 °C; 10 Min,0 °C1.3 0 °C -> Rt; 10 H,Rt1.4 Solvents: Methanol; 10 Min,Rt
标题:Selective S-Deacetylation Inspired By Native Chemical Ligation: Practical Syntheses Of Glycosyl Thiols And Drug Mercapto-Analogs
作者:Shu,Penghua; Zeng,Jing; Tao,Jinyi; Zhao,Yueqi; Yao,Guangmin; Et Al
参考文献:Green Chemistry 日期:2015 卷标:17(4) 页码:2545-2551]

4098-06-0 = 80040-79-5
反应条件:1.1 Reagents: Sodium Methoxide Solvents: Methanol; 3 H,0 °C1.2 Reagents: Sodium Hydride Solvents: Dimethylformamide; 0 °C; 20 Min,0 °C1.3 0 °C; Overnight,0 °C1.4 Reagents: Ammonium Chloride Solvents: Water
标题:Palladium Catalyzed Stereocontrolled Synthesis Of C-Aryl Glycosides Using Glycals And Arenediazonium Salts At Room Temperature
作者:Singh,Adesh Kumar; Kandasamy,Jeyakumar
参考文献:Organic & Biomolecular Chemistry 日期:2018 卷标:16(28) 页码:5107-5112

(2R,3S,4S)-3,4-Bis(Benzyloxy)-2-((Benzyloxy)Methyl)-5-Iodo-3,4-Dihydro-2H-Pyran置于disodium Hydrogenphosphate,三丁基膦体系中,用硝基甲烷,水作为反应溶剂,化学反应 1.5H,反应生成 3,4,6-三邻苄基半乳醛
参考文献:Phosphine-Free Suzuki-miyaura Cross-Coupling In Aqueous Media Enables Access To 2-C-Aryl-Glycosides
标题:Phosphine-Free Suzuki-miyaura Cross-Coupling In Aqueous Media Enables Access To 2-C-Aryl-Glycosides
摘要:A General Strategy For The Synthesis Of 2-Aryl-Glycals And Their Elaboration To 2-C-Aryl-Alpha-Glycosides And 1,5-Anhydro-2-C-Ary1-2-Deoxy Alditols Are Described. The Use Of Reliable,Efficient Phosphine-Free Suzuki-Miyaura Cross-Coupling Of 2-Iodoglycals In Aqueous Media As A Key Step Proceeds With Complete Regioselectivity At C-2 And Enables Access To 2-Aryl-Glycals With Different Configurations In Excellent Yields.
DOI:10.1021/ol3003139

海关参考信息

2901210000-乙烯
2901220000-丙烯
2902300000-甲苯
2905122000-异丙醇
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-9834515-B2
优先权日:2014-05-09
标题 :Process for synthesis of piperidine alkaloids
发明人：BHATTACHARYA ASISH KUMAR; CHAND HEMENDER RAMI
权利人:COUNCIL SCIENT IND RES
摘要:The present invention discloses a process for synthesis of piperidine alkaloids selected from fagomine, 4-epi-fagomine and nojirimycin from tri-O-benzyl-D-glucal or tri-O-benzyl-D-galactal.

专利号:US-4935503-A
优先权日:1988-05-05
标题:Azidochlorination and diazidization of glycals
发明人：NAICKER SELVARAJ; NOUJAIM ANTHONY A
权利人:BIOMIRA INC
摘要:The invention describes a one-pot single step procedure for the azidochlorination or diazidization of glycals, including glycal elements of carbohydrates. Compounds such as 3,4,6-tri-O-benzyl-2-azido-2-deoxy-alpha-D-galactopyranosy chloride, and 3,4,6-tri-O-benzyl-2-azido-2-deoxy-alpha-,beta-D-galactopyranose are prepared from tri-O-benzyl galactal as well as 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-alpha-galactopyranasol chloride and 3,6-di-O-acetyl-4-O-[2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl]-2-azido-2-deoxy-alpha-D-glycopyranosyl chloride from their respective O-acetylated glycal derivatives by the addition of azido chloride which is chemically generated in situ. A method using 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl chloride for the synthesis of antigenic determinants such as the terminal asialo GM 1 (beta-D-Gal (1->3)-beta-D-GalNAc-OR) has been demonstrated. The conversion of the subject synthon into 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide and 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose is also described. A further method for the synthetic generation of the Tn antigen (alpha-D-GalNAc-O-L-serine) is also described.

专利号:US-10774043-B2
优先权日:2016-05-06
标题 :Glycolactam compounds, process for preparation and uses thereof
发明人：BHATTACHARYA ASISH KUMAR; CHAND HEMENDER RAMI
权利人:COUNCIL SCIENT IND RES
摘要:The present invention discloses compounds of Formula I, n nwherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are independently selected from H, OBn, OH, CH 2 OBn, CH 2 OH, CH 3 ; R 9 is selected from alkyl, substituted alkyl, hydroxyl alkyl, alkenyl, benzyl; process for preparation of N-alkylated glycolactam compounds of Formula I and their use for the synthesis of piperidine alkaloids and their analogues.

专利号:WO-2015170339-A1
优先权日:2014-05-09
标题:A process for synthesis of piperidine alkaloids

专利号:US-2017267636-A1
优先权日:2014-05-09
标题:A process for synthesis of piperidine alkaloids

专利号:CN-102382081-A
优先权日:2011-09-19
标题:Synthesis method of anti-tumor active natural product jaspine B and key intermediate of 3-epi jaspine B

其他信息查阅

北京凯森莱科技有限公司

网址: http://www.chemsynlab.com
电话: 010-51184589👤

⚠️ 未注册 · 未认证企业

备注: 📌 数据来源说明：本展台内容基于各搜索引擎等公开数据整理，仅作展示用途。请用户自行辨别 ✉️ 若企业需抹除展台内容或有异议，请通过页面底部联系方式告知我们，我们会尽快处理。

第 1 / 1 页

现货

供应商参考报价(招募中)

品牌试剂参考报价(招募中)

实用工具

📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

合成参考文献

摘要:von Angerer, S., Science of Synthesis, (2005) 26, 108.
摘要:Kibayashi, C.; Yamazaki, N., Science of Synthesis, (2007) 30, 34.
摘要:Kryczka, B.; Lewkowski, J.; Zawisza, A., Science of Synthesis, (2007) 29, 976.
摘要:Merino, P., Science of Synthesis, (2007) 29, 721.
摘要:Robina, I.; Vogel, P., Science of Synthesis, (2008) 37, 780.