CAS: 93379-49-8; ((4S,5S)-2,2-Dimethyl-1,3-Dioxolane-4,5-Diyl)Bis(Diphenylmethanol)

该化合物是因其在非对称合成和催化中的作用而得到广泛承认的手性化合物,具有硫醚功能组,其特点是能够形成稳定的金属离子复合体,使其在发展手性催化剂中具有价值.该化合物一般是无色的,可视其形态和纯度而存在于黄色液体或固体中.其立体化学学,以(S,S)配置为标志,有助于其在各种化学反应中独特的再活动性和选择性,特别是在对应选择性变异中.TADDOL衍生物经常用于合成制药和农用化学品,因为它们有能力促进形成手性中心的形成.此外,(S,S)-TADDOL以其毒性和环境影响相对较低而闻名,因此在绿色化学应用中是一种有利的选择.

英文名称((4S,5S)-2,2-Dimethyl-1,3-Dioxolane-4,5-Diyl)Bis(Diphenylmethanol)
中文名称(+)-4,5-双[羟基(二苯基)甲基]-2,2-二甲基-1,3-二氧戊环
IUPAC名称((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)
其它别名(2S,3S)-(-)-4,5-Bis(diphenylhydroxymethyl)-2,2-dimethyl-1,3-dioxolane; (4S,5S)-4,5-Bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane; 1,1,4,4-Tetraphenyl-2,3-O-isopropylidene-L-threitol
CAS编号93379-49-8
MFCD编号:MFCD00010079
分子式:C31H30O4
分子量:466.57
产品CID: 1973082
产品分类化学试剂 → 有机试剂 → 膦配体

相似结构搜索
InChIKey: OWVIRVJQDVCGQX-NSOVKSMOSA-N
RNSJHECWLNVNFE-LOYHVIPDSA-N…
计算化学: 氢键受体数4.0氢键供体数2.0可旋转键数6.0

MSDS等安全信息

GHS符号GHS07
警示词Warning
危险描述H317-H319
防范说明P280-P305+P351+P338
UN编号NONH for all modes of transport
危险品标志Xn
安全声明26-36
危险类别码20/21/22-36/37/38
WGK Germany3

上下游产品

(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate bromobenzene (+)-dimethyl-2,3-O-isopropylidene-D-tartrate [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1-methyl-1H-pyridin-2-one [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1,5-dimethyl-1H-pyridin-2-one [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1,6-dimethyl-1H-pyridin-2-one [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1,4-dimethyl-1H-pyridin-2-one

合成工艺路线路线简述

100-59-4 + 167282-09-9 = 93379-49-8
反应条件:1.1 Solvents: Tetrahydrofuran; 30 Min,0 °C; Overnight,Rt1.2 Reagents: Ammonium Chloride Solvents: Water; Rt
标题:Charge-Activated Taddols: Recyclable Organocatalysts For Asymmetric (Hetero-)Diels-Alder Reactions
作者:Riegel,George F.; Takashige,Keiji; Lovstedt,Alex; Kass,Steven R.
参考文献:Journal Of Physical Organic Chemistry 日期:2022 卷标:35(9)]

87-91-2 + 77-76-9 = 93379-49-8
反应条件:1.1 Catalysts: P-Toluenesulfonic Acid Solvents: Benzene; Reflux1.2 -
标题:Selective Synthesis By Using Crystal Field And Various Asymmetric Field
作者:Sugiyama,Kunio
参考文献:Nihon Daigaku Seisan Kogakubu Haiteku Risachi Senta Kenkyu Hokokusho 日期:2004 卷标:2]

= 93379-49-8 [标题:Reaction Conditions
标题:Atroposelective Kinetic Resolution Of 8H-Indeno[1,2-C]Thiophen-8-Ols Via Pd-Catalyzed C-C Bond Cleavage Reaction
作者:Xi,Junwei; Yang,Han; Li,Lin; Zhang,Xue; Li,Chunyu; Et Al
参考文献:Organic Letters 日期:2022 卷标:24(12) 页码:2387-2392]

= 93379-49-8 [标题:Reaction Conditions
标题:Rearrangement Of Homoallylic Alcohols Induced By Dast
作者:Canova,Sophie; Bellosta,Veronique; Mignani,Serge; Bigot,Antony; Cossy,Janine
参考文献:Organic Letters 日期:2006 卷标:8(10) 页码:2091-2094]

= 93379-49-8 [标题:Reaction Conditions
标题:Asymmetric Alkylation Catalyzed By Chiral Alkali Metal Alkoxides Of Taddol. Synthesis Of α-Methyl Amino Acids
作者:Belokon,Yu. N.; Kochetkov,K. A.; Churkina,T. D.; Ikonnikov,N. S.; Chesnokov,A. A.; Et Al
参考文献:Russian Chemical Bulletin (Translation Of Izvestiya Akademii Nauk 日期:1999 卷标:48(5) 页码:917-923]

= 93379-49-8 [标题:Reaction Conditions
标题:Formation Of Racemic Compound Crystals By Mixing Of Two Enantiomeric Crystals In The Solid State. Liquid Transport Of Molecules From Crystal To Crystal
作者:Toda,Fumio; Tanaka,Koichi; Miyamoto,Hisakazu; Koshima,Hideko; Miyahara,Ikuko; Et Al
参考文献:Journal Of The Chemical Society 日期:1997 卷标:(9) 页码:1877-1885]

= 93379-49-8 [标题:Reaction Conditions
标题:Synthesis Of Tetraaryl 1,4-Diol Chiral Ligands
作者:Pei,Wen
参考文献:Yanbian Daxue Xuebao 日期:1996 卷标:22(4) 页码:26-28]

= 93379-49-8 [标题:Reaction Conditions
标题:Resolution Of Organic Compounds Via Inclusion Complexes With Trans-2,2-Dimethyl-α,α,α',α'-Tetraphenyl-1,3-Dioxolane-4,5-Dimethanol
参考文献:Japan]

2622-05-1 + 140462-73-3 = 93379-49-8 + 112897-09-3
反应条件:1.1 Reagents: Diisobutylaluminum Hydride Solvents: Dichloromethane,Toluene; -78 °C; 1 H,-78 °C1.2 Reagents: Potassium Sodium Tartrate Solvents: Ethyl Acetate,Water; -78 °C; 2 H,-78 °C1.3 Solvents: Diethyl Ether,Tetrahydrofuran; 0 °C; 2 H,0 °C; 0 °C -> -78 °C1.4 Solvents: Diethyl Ether; 18 H,-78 °C1.5 Reagents: Water; -78 °C; -78 °C -> Rt; 24 H,Rt
标题:Synthetic Approach To Wortmannilactone C
作者:Brandt,Damien; Dittoo,Aurelia; Bellosta,Veronique; Cossy,Janine
参考文献:Organic Letters 日期:2015 卷标:17(4) 页码:816-819]

73346-73-3 = 93379-49-8
反应条件:1.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran; 2 H,Reflux; Reflux -> Rt1.2 Solvents: Tetrahydrofuran; 12 H,Reflux; Reflux -> Rt1.3 Reagents: Hydrochloric Acid,Ammonium Chloride Solvents: Water; Rt
标题:Chiral Aluminum Complex Controls Enantioselective Nickel-Catalyzed Synthesis Of Indenes: C-Cn Bond Activation
作者:Zhang,Tao; Luan,Yu-Xin; Zheng,Su-Juan; Peng,Qian; Ye,Mengchun
参考文献:Angewandte Chemie 日期:2020 卷标:59(19) 页码:7439-7443]

73346-73-3 = 93379-49-8
反应条件:1.1 Reagents: Magnesium,Iodine Solvents: Tetrahydrofuran; Reflux
标题:Ni-Al Bimetallic Catalyzed Enantioselective Cycloaddition Of Cyclopropyl Carboxamide With Alkyne
作者:Liu,Qi-Sheng; Wang,De-Yin; Yang,Zhi-Jun; Luan,Yu-Xin; Yang,Jin-Fei; Et Al
参考文献:Journal Of The American Chemical Society 日期:2017 卷标:139(50) 页码:18150-18153]

93379-49-8 = 93379-49-8
反应条件:1.1 Reagents: Sodium Aluminum Hydride Solvents: Tetrahydrofuran; Rt; 5 Min,Rt
标题:Chiral Hydride Complexes
参考文献:World Intellectual Property Organization]

73346-73-3 = 93379-49-8
反应条件:1.1 Solvents: Tetrahydrofuran
标题:Design Of A New Chiral Host Compound,Trans-4,5-Bis(Hydroxydiphenylmethyl)-2,2-Dimethyl-1,3-Dioxacyclopentane. An Effective Optical Resolution Of Bicyclic Enones Through Host-Guest Complex Formation
作者:Toda,Fumio; Tanaka,Koichi
参考文献:Tetrahedron Letters 日期:1988 卷标:29(5) 页码:551-4]

= 93379-49-8 [标题:Reaction Conditions
标题:Asymmetric Ptc C-Alkylation Catalyzed By Chiral Derivatives Of Tartaric Acid And Aminophenols. Synthesis Of (R)- And (S)-α-Methyl Amino Acids
作者:Belokon,Yuri N.; Kochetkov,Konstantin A.; Churkina,Tatiana D.; Ikonnikov,Nikolai S.; Chesnokov,Alexey A.; Et Al
参考文献:Journal Of Organic Chemistry 日期:2000 卷标:65(21) 页码:7041-7048]

= 93379-49-8 [标题:Reaction Conditions
标题:Large-Scale Preparation Of α,α,α',α'-Tetraaryl-1,3-Dioxolane-4,5-Dimethanol Derivatives (Taddols),Useful Auxiliaries For Enantioselective Synthesis And Their Structure In The Solid State
作者:Beck,Albert K.; Bastani,Bahram; Plattner,Dietmar A.; Petter,Walter; Seebach,Dieter; Et Al
参考文献:Chimia 日期:1991 卷标:45 页码:238-41]

2622-05-1 + 140462-73-3 + 100-52-7 = 93379-49-8 + 85551-57-1
反应条件:1.1 Solvents: Diethyl Ether,Tetrahydrofuran1.2 Solvents: Diethyl Ether1.3 Reagents: Ammonium Fluoride Solvents: Water
标题:Enantioselective Allyltitanations And Metathesis Reactions. Application To The Synthesis Of Piperidine Alkaloids (+)-Sedamine And (-)-Prosophylline
作者:Cossy,Janine; Willis,Catherine; Bellosta,Veronique; Bouzbouz,Samir
参考文献:Journal Of Organic Chemistry 日期:2002 卷标:67(7) 页码:1982-1992]

6088-88-6 + 155089-06-8 + 140462-73-3 = 93379-49-8
反应条件:1.1 Solvents: Diethyl Ether,Tetrahydrofuran; -78 °C; 10 Min,-78 °C; 3 H,0 °C; 0 °C -> -78 °C1.2 Solvents: Diethyl Ether; -78 °C; 20 H,-78 °C1.3 Solvents: Water; -78 °C; 48 H,Rt; 16 H,0 °C
标题:Synthesis Of A Platform To Access Bistramides And Their Analogues
作者:Commandeur,Malgorzata; Commandeur,Claude; Cossy,Janine
参考文献:Organic Letters 日期:2011 卷标:13(22) 页码:6018-6021

以四氢呋喃作为反应溶剂,化学反应 12.0H,反应生成 (4S,5S)-(2,2-二甲基-1,3-二氧戊环-4,5-二基)双(二苯基甲醇)
参考文献:手性铝络合物控制茚的对映选择性镍催化的合成:C-Cn键活化.
标题:手性铝络合物控制茚的对映选择性镍催化的合成:C-Cn键活化.
摘要:开发了一种手性铝络合物控制的,对映体选择性镍催化的芳基腈和炔烃通过c-Cn键活化进行的多米诺骨牌反应.在温和的反应条件下,该反应提供了带有手性全碳四元季中心的各种茚并基,产率为32%至91%,Ee值在73%至98%之间.通过dft计算研究了立体控制的反应机理和方面.
DOI:10.1002/anie.202001142

海关参考信息

2902600000-乙苯
2905122000-异丙醇
2905310000-1,2-乙二醇
2905320000-1,2-丙二醇
💡 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-2012289733-A1
优先权日:2011-05-11
标题 :Novel borate derivatives and their applications
发明人：HEISE GLENN L; MYSLINSKA MALGORZATA
权利人:HEISE GLENN L; MYSLINSKA MALGORZATA; ANDERSON DEV CO
摘要:Borates, compositions comprising chiral (cyclic and acyclic) and achiral (cyclic and acyclic) borates; chiral (cyclic and acyclic) and achiral (cyclic and acyclic) biborates; and methods for their synthesis. Additionally, a significantly improved synthetic protocol for the synthesis of wide range of boronates starting from borates or biborates and Grignard or organolithium reagents that can be used for kilo lab and commercial scale production.

专利号:US-11286270-B2
优先权日:2017-10-11
标题:Boronic acid derivatives and synthesis thereof
发明人：HECKER SCOTT J; BOYER SERGE HENRI; DIELEMANS HUBERTUS J A; GONZALEZ DE CASTRO ANGELA; DE VRIES ANDREAS H M; LEFORT LAURENT
权利人:QPEX BIOPHARMA INC
摘要:Disclosed herein are antimicrobial compounds compositions, pharmaceutical compositions, the method of use and preparation thereof. Some embodiments relate to boronic acid derivatives and their use as therapeutic agents, for example, Î²-lactamase inhibitors (BLIs).

专利号:US-6090950-A
优先权日:1996-08-23
标题 :Chiral hydride complexes
发明人：HEISE GLENN L
权利人:ZEELAND CHEMICALS INC
摘要:Novel chiral boron and aluminum hydride complexes, compositions comprising the chiral hydride complexes, and methods for their synthesis and use are described. The novel chiral hydride complexes are of the formulas: MBH4-n-a(R*)n(R')a; MBH2-b(R**) (R')b; MBH(R***); MBH(R*) (R''); MAlH4-n-a(R*)n(R')a; MAlH2-b(R**)(R')b; MAlH(R***); and MAlH(R*) (R''), wherein M is Na+, Li+ or K+; each R* is independently a monodentate chiral ligand; R** is a bidentate chiral ligand; R*** is a tridentate chiral ligand; R' is a monodentate achiral ligand; R'' is a bidentate achiral ligand; n is 1-3; a is 0-2; and b is 0-1, with the proviso that n+a