CAS: 96422-52-5; (R)-6-((1R,2R)-1,2-Dihydroxy-2-Phenylethyl)-5,6-Dihydro-2H-Pyran-2-One

结构式图片

物理性质

MSDS等安全信息

上下游产品

(R)-6-((R)-2-Hydroxy-1-methoxymethoxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one (6R)-6-[(2S,3S)-3-phenyloxiran-2-yl]-5,6-dihydro-2H-pyran-2-one (R)-4-Benzenesulfonyl-6-((1R,2R)-1,2-dihydroxy-2-phenyl-ethyl)-tetrahydro-pyran-2-one (R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one 7,8-di-O-acetyl-goniodiol 4-Nitro-benzoic acid (1S,2S)-2-benzyloxy-2-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-phenyl-ethyl ester (1R,5R,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxa-bicyclo-[3.3.1]-nonan-3-one (-)-(1R,5R,7S,8R)-8-benzyloxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one

合成工艺路线路线简述

  • 163630-06-6 = 96422-52-5
    反应条件:1.1 Reagents: Acetic Acid Solvents: Water; 30 Min,80 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water
    标题:A Highly Enantioselective Total Synthesis Of (+)-Goniodiol
    作者:Tate,Edward W.; Dixon,Darren J.; Ley,Steven V.
    参考文献:Organic & Biomolecular Chemistry 日期:2006 卷标:4(9) 页码:1698-1706]

    214678-55-4 = 96422-52-5
    反应条件:1.1 Reagents: 1,8-Diazabicyclo[5.4.0]Undec-7-Ene Solvents: Dichloromethane
    标题:A Short And Efficient Total Synthesis Of The Cytotoxic (+)-Goniodiol And (+)-9-Deoxygoniopypyrone
    作者:Surivet,Jean-Philippe; Vatele,Jean-Michel
    参考文献:Tetrahedron Letters 日期:1998 卷标:39(40) 页码:7299-7300]

    110011-51-3 = 96422-52-5
    反应条件:1.1 Reagents: Water,(6R)-5,6-Dihydro-6-[(2S,3S)-3-Phenyl-2-Oxiranyl]-2H-Pyran-2-One; 24 H,60 °C
    标题:Biosynthesis-Inspired Total Synthesis Of Bioactive Styryllactones (+)-Goniodiol,(6S,7S,8S)-Goniodiol,(-)-Parvistone D,And (+)-Parvistone E
    作者:Ramesh,Perla; Rao,Tadikamalla P.
    参考文献:Journal Of Natural Products 日期:2016 卷标:79(8) 页码:2060-2065]

    1301607-72-6 = 96422-52-5
    反应条件:1.1 Catalysts: P-Toluenesulfonic Acid Solvents: Ethanol; Overnight,50 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water
    标题:An Efficient Total Synthesis Of (+)-Goniodiol
    作者:Sabitha,Gowravaram; Bhikshapathi,M.; Ranjith,N.; Ashwini,N.; Yadav,Jhillu S.
    参考文献:Synthesis 日期:2011 卷标:(5) 页码:821-825]

    473980-86-8 = 96422-52-5
    反应条件:1.1 Reagents: P-Toluenesulfonic Acid Solvents: Toluene
    标题:A Short And General Approach To The Synthesis Of Styryllactones: (+)-Goniodiol,Its Acetates And β-Trifluoromethyl Derivative,(+)-7-Epi-Goniodiol And (+)-9-Deoxygoniopypyrone
    作者:Chen,Jian; Lin,Guo-Qiang; Wang,Zhi-Min; Liu,Han-Quan
    参考文献:Synlett 日期:2002 卷标:(8) 页码:1265-1268]

    525589-82-6 = 96422-52-5
    反应条件:1.1 Reagents: Boron Tribromide Solvents: Dichloromethane; 6 H,-78 °C
    标题:A Concise Enantioselective Synthesis Of (+)-Goniodiol And (+)-8-Methoxygoniodiol Via Co-Catalyzed Hkr Of Anti-(2Sr,3Rs)-3-Methoxy-3-Phenyl-1,2-Epoxypropane
    作者:Kiran,I. N. Chaithanya; Reddy,R. Santhosh; Suryavanshi,Gurunath; Sudalai,Arumugam
    参考文献:Tetrahedron Letters 日期:2011 卷标:52(3) 页码:438-440]

    1256338-98-3 = 96422-52-5
    反应条件:1.1 Catalysts: P-Toluenesulfonic Acid Solvents: Methanol; 0 °C; 2 H,Rt
    标题:Stereoselective Total Synthesis Of Leiocarpin C And (+)-Goniodiol
    作者:Yadav,J. S.; Krishna,V. Hari; Srilatha,A.; Somaiah,R.; Reddy,B. V. Subba
    参考文献:Synthesis 日期:2010 卷标:(17) 页码:3004-3012]

    163630-06-6 = 96422-52-5
    反应条件:1.1 Reagents: Acetic Acid Solvents: Water; 0.5 H,80 °C; 80 °C -> 0 °C1.2 Solvents: Water; Ph 71.3 Reagents: Sodium Chloride Solvents: Water
    标题:A Total Synthesis Of The Styryllactone (+)-Goniodiol From Naphthalene
    作者:Banwell,Martin G.; Coster,Mark J.; Edwards,Alison J.; Karunaratne,Ochitha P.; Smith,Jason A.; Et Al
    参考文献:Australian Journal Of Chemistry 日期:2003 卷标:56(6) 页码:585-595]

    163630-06-6 = 96422-52-5
    反应条件:1.1 Reagents: Acetic Acid Solvents: Acetic Acid,Water
    标题:A Chemoenzymatic Synthesis Of The Styryllactone (+)-Goniodiol From Naphthalene
    作者:Banwell,Martin G.; Coster,Mark J.; Karunaratne,Ochitha P.; Smith,Jason A.
    参考文献:Journal Of The Chemical Society 日期:2002 卷标:(14) 页码:1622-1624]

    163630-06-6 = 96422-52-5
    反应条件:1.1 Reagents: Acetic Acid Solvents: Water
    标题:A Total Synthesis Of (+)-Goniodiol Using An Anomeric Oxygen-To-Carbon Rearrangement
    作者:Dixon,Darren J.; Ley,Steven V.; Tate,Edward W.
    参考文献:Journal Of The Chemical Society 日期:1998 卷标:(19) 页码:3125-3126]

    146173-64-0 = 96422-52-5
    反应条件:1.1 Reagents: Iron Chloride (Fecl3) Solvents: Dichloromethane; 5 H,Rt
    标题:Facile Stereoselective Syntheses Of Goniodiol,8-Epi-Goniodiol And 9-Deoxygoniopypyrone
    作者:Prasad,Kavirayani R.; Gholap,Shivajirao L.
    参考文献:Tetrahedron Letters 日期:2007 卷标:48(27) 页码:4679-4682]

    194355-07-2 = 96422-52-5
    反应条件:1.1 Reagents: Titanium Tetrachloride Solvents: Dichloromethane; 1 H,Rt
    标题:A Concise Synthesis Of (+)-Goniodiol Using A Catalytic Hetero Diels-Alder/allylboration Sequence
    作者:Deligny,Michael; Carreaux,Francois; Carboni,Bertrand
    参考文献:Synlett 日期:2005 卷标:(9) 页码:1462-1464]

    163630-06-6 = 96422-52-5
    反应条件:1.1 Reagents: P-Toluenesulfonic Acid Solvents: Methanol; Rt
    标题:The First Stereoselective And The Total Synthesis Of Leiocarpin C And Total Synthesis Of (+)-Goniodiol
    作者:Yadav,J. S.; Premalatha,K.; Harshavardhan,S. J.; Subba Reddy,B. V.
    参考文献:Tetrahedron Letters 日期:2008 卷标:49(48) 页码:6765-6767]

    163630-06-6 = 96422-52-5
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Tetrahydrofuran,Water
    标题:Stereoselective Syntheses Of (+)-Goniodiol,(-)-8-Epigoniodiol,And (+)-9-Deoxygoniopypyrone Via Alkoxyallylboration And Ring-Closing Metathesis
    作者:Ramachandran,P. Veeraraghavan; Chandra,J. Subash; Reddy,M. Venkat Ram
    参考文献:Journal Of Organic Chemistry 日期:2002 卷标:67(21) 页码:7547-7550
📜D-扁桃酸置于吡啶,咪唑,盐酸,4-二甲氨基吡啶,重铬酸吡啶,4 A Molecular Sieve,四丁基氟化铵,Sodium Acetate,二异丁基氢化铝,对甲苯磺酸,1,8-二氮杂双环[5.4.0]十一碳-7-烯体系中,用 四氢呋喃,甲醇,乙醚,二氯甲烷,甲苯 作为反应溶剂,化学反应 144.6H,反应生成 哥纳香二醇; (6R)-6-[(1R,2R)-1,2-二羟基-2-苯基乙基]-5,6-二氢-2H-吡喃-2-酮
参考文献:使用催化杂 Diels-Alder/烯丙基硼化序列的 (+)-Goniodiol 的简明合成
标题:使用催化杂 Diels-Alder/烯丙基硼化序列的 (+)-Goniodiol 的简明合成
摘要:报道了使用催化不对称杂 Diels-Alder/烯丙基硼化序列的 (+)-Goniodiol 的新的短而有效的合成.
DOI:10.1055/s-2005-868518

海关参考信息

专利信息


专利号:US-12240810-B2
优先权日:2019-02-04
标 题:Chiral-substituted poly-N-vinylpyrrolidinones and complexes with bimetallic nanoclusters and uses thereof in asymmetric oxidation reactions
发明人：HUA DUY H
权利人:UNIV KANSAS STATE; KANSAS STATE UNIV RESEARCH
摘要:Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a bimetallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The catalytic complexes have exhibited the ability to achieve reaction products have a very high degree of optical purifies. These reaction products can be used as reagents in the synthesis of complex organic molecules, such as bioactive products, and C—H bond oxidation of complex molecules including various drugs and natural products.

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主要参考文献

参考标题:Stereoselective And Facile Total Synthesis Of (+)-Goniodiol, A Styryllactone From Carbohydrates
作者:Jhillu Singh Yadav,Saibal Das,Anand Kumar Mishra |发布日期:2010.10
摘要:The Stereoselective Synthesis Of (+)-Goniodiol, A Cytotoxic Styryllactone, Has Been Accomplished In 10 Steps Starting From Inexpensive And Readily Available D-Manitol And δ-Gluconolactone Involving The Direct And Straightforward Reaction Conditions Of Grignard Addition, Chain Elongation, And Hydroboration, Thus Making The Synthesis Simple And Convenient.

合成参考文献


参考文献:10.1055/s-2007-990866
摘要:Prasad K, Dhaware M. Stereoselective Total Synthesis of Bioactive Styryllactones: 9-Deoxygoniopypyrone, Goniopypyrone and 7-epi-Goniofufurone. Synthesis. 2007 Dec;2007(23):3697–705. doi: 10.1055/s-2007-990866.
参考文献:10.1055/s-0030-1257858
摘要:Yadav J, Krishna V, Srilatha A, Somaiah R, Reddy B. Stereoselective Total Synthesis of Leiocarpin C and (+)-Goniodiol. Synthesis. 2010 Jul 30;2010(17):3004–12. doi: 10.1055/s-0030-1257858.
参考文献:10.1055/s-0035-1560378
摘要:Hilt G, Röse P. Cobalt-Catalysed Bond Formation Reactions; Part 2. Synthesis. 2015 Dec 03;48(04):463–92. doi: 10.1055/s-0035-1560378.
参考文献:10.1016/j.phymed.2004.07.010
摘要:Tian Z, Chen S, Zhang Y, Huang M, Shi L, Huang F, Fong C, Yang M, Xiao P. The cytotoxicity of naturally occurring styryl lactones. Phytomedicine. 2006 Feb;13(3):181–6. doi: 10.1016/j.phymed.2004.07.010.
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