CAS: 90776-59-3; (4R,5R,6S)-4-Nitrobenzyl 3-((Diphenoxyphosphoryl)Oxy)-6-((R)-1-Hydroxyethyl)-4-Methyl-7-Oxo-1-Azabicyclo[3.2.0]Hept-2-Ene-2-Carboxylate

该化合物是一种多用途有机磷化合物,与传统磷酸盐相比,其热稳定性和水解灵敏度提高,其独特结构提高了有机溶剂的溶性,使之适合于需要精确控制化学反应性和稳定性的应用.

英文名称(4R,5R,6S)-4-Nitrobenzyl 3-((Diphenoxyphosphoryl)Oxy)-6-((R)-1-Hydroxyethyl)-4-Methyl-7-Oxo-1-Azabicyclo[3.2.0]Hept-2-Ene-2-Carboxylate
中文名称4-硝基苄基(4R,5R,6S)-3-((二苯氧基磷酰基)氧基)-6-((R)-1-羟乙基)-4-甲基-7-氧代-1-氮杂双环[3.2.0] 2-烯-2-羧酸盐
IUPAC名称4-nitrobenzyl (4R,5R,6S)-3-((diphenoxyphosphoryl)oxy)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
其它别名美罗培南主环; Pnb(4R,5S,6S)-3-(Diphenyl-Oxy)Phosphoryloxy-6-[(1R)-1-Hydroxyethyl]-4-Methyl-7-Oxo-1-Azabicyclo[3,2,0]Hept-2-Ene-2-Carboxylate
CAS编号90776-59-3
MFCD编号:MFCD01318092
EINECS号:618-646-2
FDA UNII编号:0O0V6A80W3
分子式:C29H27N2O10P
分子量:594.51
产品CID: 1941374
产品分类有机原料→分子砌块→芳环类化合物→苯类化合物

相似结构搜索
产品信息参考
InChIKey: STULDTCHQXVRIX-PIYXRGFCSA-N
STULDTCHQXVRIX-PIYXRGFCSA-N…
计算化学: 氢键受体数10.0氢键供体数1.0可旋转键数11.0

物理性质

熔点129-131 °C
沸点722.4±60.0 °C at 760 mmHg
闪点390.7±32.9 °C
密度1.5±0.1 g/cm3
pKa:14.36±0.20(预测)
PSA:154.74
LogP:4.9898
折射率1.653
蒸汽压0.0±2.5 mmHg at 25°C
溶解性Chloroform (Slightly), Methanol (Slightly)
外观形态白色至类白色固体
储存条件密封干燥,2-8°C
产品应用该化合物用于抗菌剂.

MSDS等安全信息

GHS象形图
GHS符号GHS07;
注释: Exclamation mark
危险类别急性毒性类别4(经口)
皮肤致敏类别1
警示词Warning(警告)
危险描述H302 |吞咽有害.
H317 |可能引起皮肤过敏反应.
防范说明P260-P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501
危险品标志Xi
安全声明H303May be harmful if swallowed+H313Skin contact may be harmful+H333Inhalation may be harmful to the body

欧盟法规

C&L通报REACH预注册

上下游产品

(2R,4R,5R,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester chlorophosphoric acid diphenyl ester (R)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid Acetic acid (2R,3R)-3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-1-trimethylsilanyl-azetidin-2-yl ester(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-(pyrrolidine-1-carbonylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-(piperidine-1-carbothioylsulfanyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-((2R,3R,4R)-2-hydroxymethyl-4-methoxycarbonyl-oxetan-3-ylsulfanyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (4R,5S,6S)-3-((2R,3R,4R)-2-Dimethylcarbamoyl-4-hydroxymethyl-oxetan-3-ylsulfanyl)-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

合成工艺路线路线简述

2524-64-3 + 90822-24-5 = 90776-59-3
反应条件:1.1 Catalysts: 4-(Dimethylamino)Pyridine,Copper Bromide (Cubr),Octanoic Acid,Rhodium Salt (1:?) Solvents: Dichloromethane; Rt -> Reflux1.2 Reagents: Diisopropylethylamine Solvents: Dichloromethane; -25 °C
标题:Method For Preparing β-Methylcarbapenem Antibiotic Mother Nucleus
参考文献:China]

2524-64-3 + 90822-24-5 = 90776-59-3
反应条件:1.1 Catalysts: Rhodium,Tetrakis[μ-(Octanoato-Ko:Ko′)]Di-,(Rh-Rh) Solvents: Dichloromethane; 4 H,Reflux; Reflux -> -15 °C1.2 Reagents: Diisopropylethylamine Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; 50 Min,-15 °C
标题:A Preparation Method Of A Key Intermediate For The Synthesis Of 1β-Methylcarbapenems
作者:Takahashi,Masaaki; Ito,Nobuo; Kikuchi,Shunji; Yamaguchi,Hitoshi; Okue,Masayuki
参考文献:Meiji Seika Kenkyu Nenpo 日期:2008 卷标:46 页码:33-40]

2524-64-3 + 104873-15-6 = 90776-59-3
反应条件:1.1 Reagents: Diisopropylethylamine Solvents: Acetonitrile; 0 °C; 1 H,0 °C
标题:Synthesis Of 1β-Methylcarbapenems Bicyclic Nucleus
作者:Zhang,Ling; Liu,Yi; Liu,Ling; Ni,Shanhong; Li,Jian
参考文献:Zhongguo Yiyao Gongye Zazhi 日期:2010 卷标:41(12) 页码:891-894]

2524-64-3 + 110398-07-7 = 90776-59-3
反应条件:1.1 Reagents: Diisopropylethylamine Catalysts: 4-(Dimethylamino)Pyridine Solvents: Methyl Acetate; 15 - 25 °C
标题:Semicontinuous Process For Gmp Manufacture Of A Carbapenem Intermediate Via Carbene Insertion Using An Immobilized Rhodium Catalyst
作者:Gage,James R.; Chen,Furong; Dong,Changming; Gonzalez,Miguel A.; Jiang,Yong; Et Al
参考文献:Organic Process Research & Development 日期:2020 卷标:24(10) 页码:2025-2033

(3S,4R)-3-<(1R)-1-Hydroxyethyl>-4-<(1R)-1-Methyl-3-P-Nitrobenzyloxycarbonyl-2-Oxopropyl>-2-Azetidin-2-One置于辛酸铑三乙胺,N,N-二异丙基乙胺,Zinc(II) Iodide体系中,用乙酸乙酯,丙酮,甲苯作为反应溶剂,化学反应生成杂氮双环磷酸酯
参考文献: An Improved Process For The Preparation Of Meropenem[fr] Procédé Amélioré Pour La Préparation De Méropénem
标题: An Improved Process For The Preparation Of Meropenem[fr] Procédé Amélioré Pour La Préparation De Méropénem
摘要:本发明提供了一种改进的工艺,用于制备公式(i)的甲基碳青霉烯衍生物或其药用可接受的盐或水合物,且为纯净形式.

专利信息

专利号:US-8093378-B2
优先权日:2006-04-28
标题 :Crystallization method for intermediates of carbapenem antibiotics
发明人：NISHINO KEITA; KOGA TERUYOSHI; FUKAE MASAFUMI; UEDA YASUYOSHI
权利人:NISHINO KEITA; KOGA TERUYOSHI; FUKAE MASAFUMI; UEDA YASUYOSHI; KANEKA CORP
摘要:An improved crystallization method for an azetidinone compound represented by the formula 1: , which is extremely useful as a common intermediate for the synthesis of 1Î²-methylcarbapenem compounds. The present method provides crystals having higher quality and stability than conventional crystals and excellent filterability at the time of recovery; and an azetidinone compound having a low content of impurity, and which has a controlled particle size distribution of crystals and improved handleability and stability. The crystallization is carried out by adding a hydrocarbon solvent to a solution in which an azetidinone compound extremely useful as a common intermediate for the synthesis of 1Î²-methylcarbapenem compounds is dissolved in the presence of a seed crystal in an amount of 200% by weight or less based on the weight of the azetidinone compound.

专利号:WO-2024254278-A9
优先权日:2023-06-08
标题 :Ophthalmic films
发明人：BANERJEE AMRITA; MITRAGOTRI SAMIR; LEVINSON DOUGLAS
权利人:FOUNT BIO INC
摘要:The present application describes the synthesis, formulation and uses of systems comprising conjugates or materials prepared therefrom, capable of retaining systems on the ocular surface.

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