CAS: 83-87-4; (3R,4S,5R,6R)-6-(Acetoxymethyl)Tetrahydro-2H-Pyran-2,3,4,5-Tetrayl Tetraacetate

该化合物是D-甘甘糖的衍生物,所有5个羟基组都是乙基的,导致完全乙基糖.该化合物的特点是分子结构,包括一个丙烯酸环,一种六人环状甘蔗糖,以及附于羟基位置的5个乙酰组.乙酸盐会增强分子的亲脂性,使其与其母糖相比更极性,从而影响其溶解性和再活性.D-甘基甲酸五乙酸盐通常是白色的,与非白晶状固体有关,在氯仿和丙酮等有机溶剂中是可溶的,但因存在大乙基酸组而较少溶于水中.这种化合物经常用于有机合成,并用作各种石基边和其他碳水化合物衍生物的中间体,从而影响其溶液性和再活性.此外,D-甘基五丙酸酯一般是白色至非白晶体固体固体固体的固体反应,在同质化学的模型研究中可以用作.

结构式图片

物理性质

MSDS等安全信息

上下游产品

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合成工艺路线路线简述

  • 492-62-6 = 83-87-4
    反应条件:1.1 Reagents: Perchloric Acid Solvents: Acetic Anhydride; 0 °C; 5 H,0 °C
    标题:Visible Light-Induced Sulfonylation/arylation Of Styrenes In A Double Radical Three-Component Photoredox Reaction
    作者:Lipp,Benjamin; Et Al
    参考文献:Chemistry - A European Journal 日期:2019 卷标:25(38) 页码:8965-8969]

    492-62-6 = 83-87-4
    反应条件:1.1 Reagents: Pyridine; 16 H,Rt
    标题:Facile And Versatile Chemoenzymatic Synthesis Of Enterobactin Analogues And Applications In Bacterial Detection
    作者:Lee,Albert A.; Et Al
    参考文献:Angewandte Chemie 日期:2016 卷标:55(40) 页码:12338-12342]

    2280-44-6 = 83-87-4
    反应条件:1.1 Catalysts: 2396751-38-3; 14 H,Rt
    标题:Coinage Metal (Bisfluorosulfonyl)Imide Complexes: Preparation,Characterization,And Catalytic Applications
    作者:Tang,Yu; Et Al
    参考文献:European Journal Of Inorganic Chemistry 日期:2020 卷标:2020(1) 页码:107-118]

    498-07-7 = 83-87-4
    反应条件:1.1 Catalysts: Scandium Triflate1.2 Reagents: Methanol
    标题:Sc(Otf)3-Catalyzed Acetolysis Of 1,6-Anhydro-β-Hexopyranoses And Solvent-Free Per-Acetylation Of Hexoses
    作者:Lee,Jinq-Chyi; Et Al
    参考文献:Tetrahedron Letters 日期:2002 卷标:43(5) 页码:851-855]

    50-99-7 = 83-87-4
    反应条件:1.1 Catalysts: Titania,Tungstate(4-),[μ12-[orthosilicato(4-)-Ko:Ko:Ko:Ko′:Ko′:Ko′:Ko′′:Ko′′:Ko′′:Ko′′′...
    标题:Synthesis Of Glucose Pentacetate By Using Tisiw12O40/tio2 As Catalyst
    作者:Yang,Shuijin; Et Al
    参考文献:Huaxue Shijie 日期:2000 卷标:41(12) 页码:650-652]

    492-61-5 = 83-87-4
    反应条件:1.1 Reagents: Sodium Acetate Solvents: Acetic Anhydride; 4 H,90 °C
    标题:First Total Syntheses Of Two Natural Glycosides
    作者:Dong,Hongbo; Et Al
    参考文献:Carbohydrate Research 日期:2021 卷标:499]

    69127-37-3 + 71-50-1 = 83-87-4
    反应条件:1.1 Solvents: Water
    标题:Synthesis Of Tetra-O-Acetylhexoses With A Free 2-Hydroxyl Group. Synthesis Of Disaccharides
    作者:Helferich,Burckhardt; Et Al
    参考文献:Chemische Berichte 日期:1962 卷标:95 页码:2604-11]

    117252-66-1 = 83-87-4 [标题:Reaction Conditions
    标题:2-(Trimethylsilyl)Ethyl Glycosides. 3. Synthesis,Anomeric Deblocking,And Transformation Into 1,2-Trans 1-O-Acyl Sugars
    作者:Jansson,Karl; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1988 卷标:53(24) 页码:5629-47]

    40437-08-9 = 83-87-4
    反应条件:1.1 Reagents: 1,8-Diazabicyclo[5.4.0]Undec-7-Ene Catalysts: 5H-Pyrrolo[2,1-C]-1,2,4-Triazolium,6,7-Dihydro-2-(2,4,6-Trimethylphenyl)-,Chlo... Solvents: Toluene; 44 H,90 °C
    标题:Organocatalytic Conversion Of Ribose And Other Protected Carbohydrate Derivatives Into 2-Deoxy-Lactones
    作者:Wendeborn,Sebastian; Et Al
    参考文献:Synlett 日期:2012 卷标:23(4) 页码:541-544]

    492-62-6 = 83-87-4
    反应条件:1.1 Reagents: Perchloric Acid Solvents: Acetic Anhydride; 0 °C; 5 H,0 °C
    标题:Visible Light-Induced Sulfonylation/arylation Of Styrenes In A Double Radical Three-Component Photoredox Reaction
    作者:Lipp,Benjamin; Et Al
    参考文献:Chemrxiv 日期:2019 卷标:1 页码:1-4]

    50-99-7 = 83-87-4
    反应条件:1.1 Reagents: Perchloric Acid Solvents: Water; 0 °C; 5 H,0 °C
    标题:Total Synthesis Of Beshanzuenone D And Its Epimers And Abiespiroside A
    作者:Borade,Balasaheb R.; Et Al
    参考文献:Organic Letters 日期:2020 卷标:22(21) 页码:8561-8565]

    50-99-7 = 83-87-4
    反应条件:1.1 Reagents: Pyridine Catalysts: 4-(Dimethylamino)Pyridine; Overnight,0 °C1.2 Reagents: Sodium Bicarbonate
    标题:Immobilization Of Udp-Galactose On An Amphiphilic Resin
    作者:Bevan,Jessica G. M.; Et Al
    参考文献:European Journal Of Organic Chemistry 日期:2018 卷标:2018(7) 页码:908-914]

    50-99-7 = 83-87-4
    反应条件:1.1 Reagents: Sodium Acetate
    标题:Total Synthesis Of Lagerstannin C: Follow-Up Of The Khanbabaee'S Synthesis
    作者:Kaneko,Yuki; Et Al
    参考文献:Synthesis 日期:2017 卷标:49(22) 页码:5003-5006]

    54-17-1 = 83-87-4
    反应条件:1.1 Catalysts: Boric Acid (H3Bo3); 1 H,Rt -> 50 °C
    标题:Silica-Supported Boric Acid Catalyzed Synthesis Of Dihydropyrimidin-2-Ones,Bis(Indolyl)Methanes,Esters And Amides
    作者:Kumar,Vishal; Et Al
    参考文献:Indian Journal Of Chemistry 日期:2014 卷标:(1) 页码:83-89]

    54-17-1 = 83-87-4
    反应条件:1.1 Catalysts: Pyridine
    标题:Synthesis Of Glycosidic Derivatives Of Diaphenylsulfone
    作者:Zhevlakova,A. K.; Et Al
    参考文献:Izvestiya Akademii Nauk Turkmenskoi Ssr 日期:1990 卷标:(5) 页码:68-73]

    13242-55-2 = 83-87-4
    反应条件:1.1 Catalysts: Scandium Triflate1.2 Reagents: Methanol
    标题:Sc(Otf)3-Catalyzed Acetolysis Of 1,6-Anhydro-β-Hexopyranoses And Solvent-Free Per-Acetylation Of Hexoses
    作者:Lee,Jinq-Chyi; Et Al
    参考文献:Tetrahedron Letters 日期:2002 卷标:43(5) 页码:851-855]

    2873-29-2 = 83-87-4
    反应条件:1.1 Reagents: Sodium Periodate Catalysts: Cerium Trichloride Solvents: Water; Rt; Rt -> 0 °C1.2 Catalysts: Ruthenium Trichloride Solvents: Acetonitrile,Ethyl Acetate; 2 Min,0 °C1.3 Solvents: Ethyl Acetate; 15 Min,0 °C1.4 Reagents: Pyridine Solvents: Pyridine
    标题:An Efficient Stereoselective Dihydroxylation Of Glycals Using A Bi-Metallic System,Rucl3/cecl3/naio4
    作者:Tiwari,Pallavi; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2006 卷标:71(7) 页码:2911-2913]

    2873-29-2 = 83-87-4
    反应条件:1.1 Reagents: Sodium Bicarbonate,Potassium Peroxymonosulfate Sulfate (2Khso5.Khso4.K2So4) Solvents: Acetone,Water; 30 - 60 Min,20 - 25 °C; Rt1.2 -
    标题:An Efficient One Step Dihydroxylation Of 1,2-Glycals With Oxone In Acetone
    作者:Rani,Shikha; Et Al
    参考文献:Tetrahedron Letters 日期:2003 卷标:44(5) 页码:907-909]

    71080-12-1 = 83-87-4
    反应条件:1.1 Reagents: Sodium,Ammonia Solvents: Tetrahydrofuran; 10 Min,-78 °C; 20 Min,-78 °C1.2 Reagents: Ammonium Chloride; -78 °C -> 25 °C; 30 Min,25 °C1.3 Reagents: 4-(Dimethylamino)Pyridine Solvents: Pyridine; 15 H,25 °C1.4 Reagents: Sodium Bicarbonate,Sodium Chloride Solvents: Water
    标题:Reducing Oligosaccharides Via Glycal Assembly: On The Remarkable Stability Of Anomeric Hydroxyl Groups To Global Deprotection With Sodium In Liquid Ammonia
    作者:Iserloh,Ulrich; Et Al
    参考文献:Tetrahedron Letters 日期:2002 卷标:43(39) 页码:7027-7030]

    127-09-3 + 50-99-7 = 83-87-4
    反应条件:1.1 Reagents: Acetic Anhydride; 4 H,Reflux1.2 Reagents: Water; Cooled
    标题:Synthesis Of Glycopolymers At Various Pendant Spacer Lengths Of Glucose Moiety And Their Effects On Adhesion,Viability And Proliferation Of Osteoblast Cells
    作者:Trinadh,Mummuluri; Et Al
    参考文献:Rsc Advances 日期:2014 卷标:4(70) 页码:37400-37410]

    127-09-3 + 50-99-7 = 83-87-4
    反应条件:1.1 Solvents: Acetic Anhydride; 4 H,90 °C
    标题:Synthesis Of Peo-Based Di-Block Glycopolymers At Various Pendant Spacer Lengths Of Glucose Moiety And Their In-Vitro Biocompatibility With Mc3T3 Osteoblast Cells
    作者:Trinadh,Mummuluri; Et Al
    参考文献:Designed Monomers And Polymers 日期:2016 卷标:19(1) 页码:24-33]

    34685-57-9 = 83-87-4 [标题:Reaction Conditions
    标题:Terpenyl Glucosides
    参考文献:Japan]

    40437-08-9 = 83-87-4
    反应条件:1.1 Reagents: Sodium Acetate; Rt
    标题:Design,Synthesis And Antitumor Study Of Novel 1,4-Bispiperazinecarbodithioic Acid [1 -Substituted-(1,2,3-Triazole)-4]-Methyl Esters
    作者:Wang,Mengmeng; Et Al
    参考文献:Youji Huaxue 日期:2013 卷标:33(11) 页码:2384-2390
📜3,4,6-Tri-O-Acetyl-1,2-O-<(R,S)-Benzylidene>-α-D-Glucopyranose置于三氟乙酸体系中,用 吡啶 作为反应溶剂,化学反应 17.0H,反应生成 1,2,3,4,6-Alpha-D-葡萄糖五乙酸酯
参考文献:A Convenient Synthesis Of 1,2-O-Benzylidene And 1,2-O-Ethylidene Derivatives Of Carbohydrates
标题:A Convenient Synthesis Of 1,2-O-Benzylidene And 1,2-O-Ethylidene Derivatives Of Carbohydrates
摘要:
DOI:10.1016/s0008-6215(00)80547-9

海关参考信息

专利信息


专利号:US-4384998-A
优先权日:1981-03-30
标题:Synthesis of thienamycin from D-glucose
发明人：DURETTE PHILIPPE L
权利人:MERCK & CO INC
摘要:Disclosed is a chiral, total synthesis of thienamycin from D-glucose which proceeds via intermediates I, II and III to known aldehyde IV which is known to be useful in the total synthesis of thienamycin (V): ##STR1## wherein: R is lower alkyl having 1-6 carbon atoms or bi-valent alkyl having 2-6 carbon atoms which joins the two sulfur atoms; R 1 is lower alkyl or aralkyl, such as benzyl and the like; and R 2 is hydrogen or a removable protecting group, such as triorganosilyl wherein the organo groups are independently selected from lower alkyl, phenyl and phenylloweralkyl.

专利号:US-4448976-A
优先权日:1981-03-30
标题 :Chiral synthesis of thienamycin from D-gluocose
发明人：DURETTE PHILIPPE L
权利人:MERCK & CO INC
摘要:Disclosed is a chiral, total synthesis of thienamycin from D-glucose which proceeds via intermediates I, II and III to known aldehyde IV which is known to be useful in the total synthesis of thienamycin (V): ##STR1## wherein: R is lower alkyl having 1-6 carbon atoms or bi-valent alkyl having 2-6 carbon atoms which joins the two sulfur atoms; R 1 is lower alkyl or aralkyl, such as benzyl and the like; and R 2 is hydrogen or a removable protecting group, such as triorganosilyl wherein the organo groups are independently selected from lower alkyl, phenyl and phenylloweralkyl.

专利号:US-4544502-A
优先权日:1981-03-30
标 题 :Chiral synthesis of thienamycin from D-glucose
发明人：DURETTE PHILIPPE L
权利人:MERCK & CO INC
摘要:Disclosed is a chiral, total synthesis of thienamycin from D-glucose which proceeds via intermediates I, II and III to known aldehyde IV which is known to be useful in the total synthesis of thienamycin (V): ##STR1## wherein: R is lower alkyl having 1-6 carbon atoms or bi-valent alkyl having 2-6 carbon atoms which joins the two sulfur atoms; R 1 is lower alkyl or aralkyl, such as benzyl and the like; and R 2 is hydrogen or a removable protecting group, such as triorganosilyl wherein the organo groups are independently selected from lower alkyl, phenyl and phenylloweralkyl.

专利号:WO-9636627-A1
优先权日:1995-05-19
标 题 :Collection of activated glycoside compounds and their biological use
发明人：ANDERSON MARK BRIAN; MUSSER JOHN H
权利人:GLYCOMED INC
摘要:The present invention relates to the field of combinatorial carbohydrate chemistry and involves the modification of organic molecules and/or the synthesis of large numbers of products comprising carbohydrate and/or glycominetic entities. More specifically, the present invention relates to activated carbon glycosides useful for the modification of organic molecules by incorporation of carbohydrate units, providing the synthesis of large numbers of products having novel chemical characteristics. The present invention further relates to methods for the generation of chemical compounds comprising carbon glycosides. Methods are disclosed to provide large arrays of molecules and to identify species that act as agonists or antagonists of various biological, chemical, and other activities.

专利号:US-6627744-B2
优先权日:1999-07-02
标 题 :Synthesis of glycodendrimer reagents
发明人：DAVIS BENJAMIN G; JONES JOHN BRYAN; BOTT RICHARD R
权利人:GENENCOR INT
摘要:The present invention relates to a chemically modified mutant protein including a cysteine residue substituted for a residue other than cysteine n a precursor protein, the substituted cysteine residue being subsequently modified by reacting the cysteine residue with a glycosylated thiosulfonate. Also a method of producing the chemically modified mutant protein is provided. The present invention also relates to a glycosylated methanethiosulfonate. Another aspect of the present invention is a method of modifying the functional characteristics of a protein including providing a protein and reacting the protein with a glycosylated methanethiosulfonate reagent under conditions effective to produce a glycoprotein with altered functional characteristics as compared to the protein. In addition, the present invention relates to methods of determining the structure-function relationships of chemically modified mutant proteins. The present invention also relates to synthetic methods for producing thio-glycoses, the thio-glycoses so produced, and to methods for producing glycodendrimer reagents.

专利号:US-2003072716-A1
优先权日:2001-06-22
标 题:Renewable, carbohydrate based CO2-philes
发明人：POOVATHINTHODIYIL RAVEENDRAN; WALLEN SCOTT L
摘要:A composition is disclosed comprising a carbohydrate-based material a dispersed in carbon dioxide. A general method for synthesizing inexpensive, renewable, non-toxic, non-fluorous, carbohydrate based CO 2 -philes is disclosed. These CO 2 -philes are soluble in carbon dioxide. Methods of making the composition are also disclosed. The methods and composition are useful in a variety of applications and can utilize gaseous, liquid and supercritical carbon dioxide. The methods and compositions are useful in the synthesis of surfactants and metal chelates for CO 2 , as a sizing substrate, in CO 2 -based coating processes, for impregnation and plasticizing cellulosic and non-cellulosic materials, in pharmaceutical applications, such as crystallization, dispersion and encapsulation of bioactive molecules in solid systems, in the densification of CO 2 , in the synthesis of biodegradable polymers in CO 2 , and for carbon dioxide removal, to name just a few.

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合成参考文献


摘要:Kryczka, B.; Lewkowski, J.; Zawisza, A., Science of Synthesis, (2007) 29, 992.
摘要:Gunn, S. J.; Warriner, S. L.; White, J. W., Science of Synthesis, (2007) 29, 909.
摘要:Kryczka, B.; Lewkowski, J.; Zawisza, A., Science of Synthesis, (2007) 29, 989.
摘要:Chemla, F.; Ferreira, F.; Roy, B., Science of Synthesis, (2007) 29, 864.
摘要:Kryczka, B.; Lewkowski, J.; Zawisza, A., Science of Synthesis, (2007) 29, 1040.
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