4-Pentenoic acid, 2-[(diphenylmethylene)amino]-, 1,1-dimethylethyl ester, (2R)-

Base Information

• Chemical Name: 4-Pentenoic acid, 2-[(diphenylmethylene)amino]-, 1,1-dimethylethyl ester, (2R)-
• CAS No.: 119244-19-8
• Molecular Formula: C₂₂H₂₅NO₂
• Molecular Weight: 335.446
• Mol file: 119244-19-8.mol

Synonyms:

Chemical Property of 4-Pentenoic acid, 2-[(diphenylmethylene)amino]-, 1,1-dimethylethyl ester, (2R)-

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Pentenoic acid, 2-[(diphenylmethylene)amino]-, 1,1-dimethylethyl ester, (2R)-

There total 15 articles about 4-Pentenoic acid, 2-[(diphenylmethylene)amino]-, 1,1-dimethylethyl ester, (2R)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) + tert-butyl allyl carbonate (70122-89-3) → tert-butyl (S)-2-[(diphenylmethylene)amino]pent-4-enoate (119244-19-8,137896-97-0,119244-22-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrakis(acetonitrile)copper(I)tetrafluoroborate; (S,S)-[2-(4'-isopropyloxazolin-2'-yl)ferrocenyl]diphenylphosphine; triethylamine; In dichloromethane; at -20 ℃; enantioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1002/adsc.201800986

Reference yield: 99.0%

→ (R)-tert-butyl 2-[(diphenylmethylene)amino]pent-4-enoate (119244-22-3,137896-97-0,119244-19-8)

Guidance literature:

Reference yield: 98.0%

Allyl acetate (591-87-7) + N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) → tert-butyl (S)-2-[(diphenylmethylene)amino]pent-4-enoate (119244-19-8,137896-97-0,119244-22-3)

Guidance literature:

With bis(η3-allyl-μ-chloropalladium(II)); C₂₉H₃₀NOPRu; copper(II) bis(trifluoromethanesulfonate); caesium carbonate; In tetrahydrofuran; at -10 ℃; enantioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1039/c7cc08732b

upstream raw materials:

N-(diphenylmethylene)glycine tert-butyl ester

allyl bromide

Allyl acetate

Benzophenone imine

Downstream raw materials:

(S)-2-allylglycine tert-butyl ester

TIPSO-D-Hpla(TIPS)-D-Leu-L-Choi(TIPS)-L-Arg(δ,ω'-di-Cbz)-OMe

TIPSO-D-Hpla(TIPS)-D-Leu-L-Choi(TIPS)-L-Argol(δ,ω'-di-Cbz)

Boc-L-Choi(TIPS)-L-Arg(δ,ω'-di-Cbz)-OMe

Refernces

• 1、 Nakoji, Masayoshi,Kanayama, Takatoshi,Okino, Tomotaka,Takemoto, Yoshiji. "Chiral phosphine-free Pd-mediated asymmetric allylation of prochiral enolate with a chiral phase-transfer catalyst". . p. 3329 - 3331. Retrieved 2001.
• 2、 Park, Hyeung-Geun,Jeong, Byeong-Seon,Yoo, Mi-Sook,Lee, Jeong-Hee,Park, Boon-Saeng,Kim, Myoung Goo,Jew, Sang-Sup. "Highly efficient ortho-fluoro-dimeric cinchona-derived phase-transfer catalysts". . p. 3497 - 3500. Retrieved 2003.
• 3、 Corey, E. J.,Xu, Feng,Noe, Mark C.. "A Rational Approach to Catalytic Enantioselective Enolate Alkylation Using a Structurally Rigidified and Defined Chiral Quaternary Ammonium Salt under Phase Transfer Conditions". . p. 12414 - 12415. Retrieved 1997.
• 4、 Woo, Seunga,Kim, Yong-Gyun,Lim, Baegeun,Oh, Jiin,Lee, Yeonji,Gwon, Hyeri,Nahm, Keepyung. "Dimeric cinchona ammonium salts with benzophenone linkers: Enantioselective phase transfer catalysts for the synthesis of α-Amino acids". . p. 2157 - 2160. Retrieved 2018.
• 5、 O'Donnell, Martin J.,Bennett, William D.,Wu, Shengde. "The Stereoselective Synthesis of α-Amino Acids by Phase-Transfer Catalysis". . p. 2353 - 2355. Retrieved 1989.
• 6、 Kitamura, Masanori,Arimura, Yuichiro,Shirakawa, Seiji,Maruoka, Keiji. "Combinatorial approach for the design of new, simplified chiral phase-transfer catalysts with high catalytic performance for practical asymmetric synthesis of α-alkyl-α-amino acids". . p. 2026 - 2030. Retrieved 2008.
• 7、 Wang, Yong-Gang,Maruoka, Keiji. "Design of chiral phase transfer catalyst with conformationally fixed biphenyl core: Application to asymmetric alkylation of glycine derivatives". . p. 628 - 632. Retrieved 2007.
• 8、 He, Wei,Wang, Quanjun,Wang, Qiaofeng,Zhang, Bangle,Sun, Xiaoli,Zhang, Shengyong. "Synthesis of novel chiral phase-transfer catalysts and their application to asymmetric synthesis of α-amino acid derivatives". . p. 1311 - 1314. Retrieved 2009.
• 9、 Hashimoto, Takuya,Maruoka, Keiji. "Substituent effect of binaphthyl-modified spiro-type chiral phase-transfer catalysts". . p. 3313 - 3316. Retrieved 2003.
• 10、 Wang, Yong-Gang,Ueda, Mitsuhiro,Wang, Xisheng,Han, Zhenfu,Maruoka, Keiji. "Convenient preparation of chiral phase-transfer catalysts with conformationally fixed biphenyl core for catalytic asymmetric synthesis of α-alkyl- and α,α-dialkyl-α-amino acids: application to the short asymmetric synthesis of BIRT-377". . p. 6042 - 6050. Retrieved 2007.