N-(Diphenylmethylene)glycine tert-butyl ester
(Synonyms: N-二苯亚甲基-甘氨酸叔丁酯) 目录号 : GC65216
N-(Diphenylmethylene)glycine tert-butyl ester 是一种染料，也是有机合成的原料和中间体。
Cas No.:81477-94-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
N-(Diphenylmethylene)glycine tert-butyl ester is a dye, also as the raw material and intermediate for organic syntheses[1][2].
[1]. Hyeung-geunPark, et al. Trimeric Cinchona alkaloid phase-transfer catalyst: α,α′,α′′-tris[O(9)-allylcinchonidinium]mesitylene tribromide. Tetrahedron Letters. Jun 2001, 42;28 4645-4648.
[2]. BernardHulin, et al. A practical synthesis of (R)- and (S)-3-amino-3,4-dihydro-1H-quinolin-2-one. Tetrahedron: Asymmetry. Jun 2004, 15;12 1957-1958.
| Cas No. | 81477-94-3 | SDF | Download SDF |
| 别名 | N-二苯亚甲基-甘氨酸叔丁酯 | ||
| 分子式 | C19H21NO2 | 分子量 | 295.38 |
| 溶解度 | 储存条件 | Store at -20°C | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.3855 mL | 16.9273 mL | 33.8547 mL |
| 5 mM | 0.6771 mL | 3.3855 mL | 6.7709 mL |
| 10 mM | 0.3385 mL | 1.6927 mL | 3.3855 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Synthetic studies on (-)-lemonomycin: an efficient asymmetric synthesis of lemonomycinone amide
J Org Chem 2009 Mar 6;74(5):2046-52.PMID:19196163DOI:10.1021/jo8027449.
Asymmetric synthesis of lemonomycinone amide (2) was accomplished from readily accessible starting materials. Enantioselective alkylation of N-(Diphenylmethylene)glycine tert-butyl ester (11) by 5-tert-butyldimethylsilyloxy-2,4-dimethoxy-3-methylbenzyl bromide (10) in the presence of Corey-Lygo's phase transfer catalyst [O-(9)-ally-N-(9'-anthracenylmethyl) cinchonidium bromide, 0.1 equiv] afforded, after chemoselective hydrolysis of the imine function (THF/H(2)O/AcOH), the substituted l-tert-butyl phenylalanate 13 in 85% yield. A Pictet-Spengler reaction of 14 with benzyloxyacetaldehyde (15) provided the 1,3-cis-disubstituted tetrahydroisoquinoline 16 in 85% yield as a single diastereomer. Coupling of hindered secondary amine 16 with amino acid 9 was accomplished under carefully controlled conditions to furnish the amide 22, which was in turn converted to hemiaminal 24. A hafnium triflate catalyzed conversion of hemiaminal to alpha-amino thioether followed by a silver tetrafluoroborate promoted intramolecular Mannich reaction of 26 afforded the tetracycle 27 in excellent overall yields. Debenzylation of 27 [Pd(OH)(2), H(2), MeOH, 0 degrees C], removal of N-Boc function (aqueous 3 N HCl, MeOH/H(2)O), and oxidation of hydroquinone to quinone [(NH(4))(2)Ce(NO(3))(6), H(2)O, rt] afforded the lemonomycinone amide 2 in 76% yield over three steps.
Diastereoselective Synthesis of Functionalized 5-Amino-3,4-Dihydro-2H-Pyrrole-2-Carboxylic Acid Esters: One-Pot Approach Using Commercially Available Compounds and Benign Solvents
Chemistry 2021 Mar 8;27(14):4573-4577.PMID:33464645DOI:10.1002/chem.202005262.
A novel three-step four-transformation approach to highly functionalized 5-amino-3,4-dihydro-2H-pyrrole-2-carboxylic acid esters, starting from commercially available phenylsulfonylacetonitrile, aldehydes, and N-(Diphenylmethylene)glycine tert-butyl ester, was developed. The one-pot strategy delivered this class of amidines bearing, for the first time, three contiguous stereocenters, in good to high yield and diastereoselectivity. The entire sequence was carried out using diethyl carbonate and 2-methyl tetrahydrofuran as benign solvents, operating under metal-free conditions. The process could be conveniently scaled-up, and the synthetic utility of the products was demonstrated.
A powerful synergistic effect for highly efficient diastereo- and enantioselective phase-transfer catalyzed conjugate additions
Chem Commun (Camb) 2011 Feb 7;47(5):1631-3.PMID:21116533DOI:10.1039/c0cc04321d.
An efficient, catalytic, diastereo- and enantioselective conjugate addition of N-(Diphenylmethylene)glycine tert-butyl ester to β-aryl substituted enones was realized in the presence of 1 mol% of newly desired dinuclear N-spiro-ammonium salts, affording functionalized α-amino acid derivatives in 57-98% yields with high diastereoselectivity (up to 99:1 dr) and enantioselectivity (up to 96.5:3.5 er).
Combinatorial design of simplified high-performance chiral phase-transfer catalysts for practical asymmetric synthesis of alpha-alkyl- and alpha,alpha-dialkyl-alpha-amino acids
Chem Asian J 2008 Sep 1;3(8-9):1702-14.PMID:18683160DOI:10.1002/asia.200800107.
A very efficient, chiral phase-transfer catalyst, (S)-2 Db, was prepared by taking advantage of the combinatorial approach from the readily available (S)-1,1'-binaphthyl-2,2'-dicarboxylic acid. This catalyst exhibited high catalytic performance (0.01-0.1 mol %) in the asymmetric alkylation of N-(Diphenylmethylene)glycine tert-butyl ester and N-(p-chlorophenylmethylene)alanine tert-butyl ester relative to other chiral phase-transfer catalysts in current use. This has created a general and highly practical procedure for the enantioselective synthesis of structurally diverse natural and unnatural alpha-alkyl-alpha-amino acids as well as alpha,alpha-dialkyl-alpha-amino acids. A similar simplified catalyst, (S)-2 Fb, is also applicable to the direct asymmetric aldol reaction between glycine Schiff base and aldehydes with moderate syn selectivity and high enantioselectivity.
Liposomes Can Achieve Enantioselective C-C Bond Formation of an α-Amino Acid Derivative in Aqueous Media
ACS Omega 2017 Jan 12;2(1):91-97.PMID:31457212DOI:10.1021/acsomega.6b00479.
We first report that a highly enantioselective C-C bond formation reaction was achieved with liposomes in aqueous media. Alkylation of N-(Diphenylmethylene)glycine tert-butyl ester (DMGBE) with benzyl bromide was conducted in the presence of cetyltrimethylammonium bromide micelles, resulting in a high conversion of DMGBE but little enantiomeric excess (e.e.) of the product. The same reaction was then carried out in 1,2-dioleoyl-sn-glycero-3-phosphocholine liposome suspensions, where the e.e. values were high (at least 90 % (S)), indicating that the liposome membranes can behave as the promoter of the enantioselective reaction. Changing the type of lipid to 1,2-dipalmitoyl-sn-glycero-3-phosphocholine to form a more ordered bilayer membrane lowered the reaction conversion but still maintained high e.e.% , that is, >90 (S), regardless of lipid chirality. It is indicated that multiple interactions between the DMGBE intermediate and lipid molecules promoted the migration of the intermediate into the interior of the membrane, whose bottom side (Si face) could be free for alkylation. These results suggest that liposomes can promote and regulate the alkylation of amino acid derivatives.