(S)-N-Boc-2-(3'-butenyl)glycine

Base Information

• Chemical Name: (S)-N-Boc-2-(3'-butenyl)glycine
• CAS No.: 208522-13-8
• Molecular Formula: C11H19NO4
• Molecular Weight: 229.276
• Mol file: 208522-13-8.mol

Synonyms:(2S)-2-[(tert-butoxycarbonyl)amino]hex-5-enoic acid;BocNH-Hag-OH;(S)-2-N-(tert-butoxycarbonyl)-2-amino-5-hexenoic acid;2-N-(tert-butoxycarbonyl)-2-aminohex-5-enoic acid;(2S)-2-tert-butoxycarbonylaminohex-5-enoate;(S)-2-((tertbutoxycarbonyl)amino)hex-5-enoic acid;(S)-N-Boc-2-(3'-butenyl)glycine;

Chemical Property of (S)-N-Boc-2-(3'-butenyl)glycine

Chemical Property:

• Boiling Point: 369.1±35.0 °C(Predicted)
• PKA: 3.96±0.10(Predicted)
• PSA: 75.63000
• Density: 1.078±0.06 g/cm3(Predicted)
• LogP: 2.32140

Purity/Quality:

98.5% ^*data from raw suppliers

(S)-N-Boc-2-(3'-butenyl)glycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-N-Boc-2-(3'-butenyl)glycine

There total 22 articles about (S)-N-Boc-2-(3'-butenyl)glycine 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%

(S)-2-tert-butoxycarbonylamino-hex-5-enoic acid methyl ester (92136-57-7) → (S)-2-N-(tert-butoxycarbonyl)-2-amino-5-hexenoic acid (208522-13-8)

Guidance literature:

With water; lithium hydroxide; In 1,4-dioxane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1007/s10593-020-02704-6

Reference yield: 74.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-(-)-1-tert-butyl-2--5-hexenoate (226985-05-3) → (S)-2-N-(tert-butoxycarbonyl)-2-amino-5-hexenoic acid (208522-13-8)

Guidance literature:

(S)-(-)-1-tert-butyl-2--5-hexenoate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 6h;

di-tert-butyl dicarbonate; With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1021/acs.orglett.1c03532

Reference yield: 64.0%

tert-butyl (S)-4-(but-3-enyl)-2,2-dimethyloxazolidine-3-carboxylate (144090-57-3) → (S)-2-N-(tert-butoxycarbonyl)-2-amino-5-hexenoic acid (208522-13-8)

Guidance literature:

With chromic acid; In water; acetone; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2014.07.045

upstream raw materials:

(S)-ethyl 2 N-(tert-butoxycarbonyl)-2-amino-5-hexenoate

(S)-2-tert-butoxycarbonylamino-hex-5-enoic acid methyl ester

di-tert-butyl dicarbonate

(RS)-ethyl 2 N-(tert-butoxycarbonyl)-2-amino-5-hexenoate

Downstream raw materials:

N-(N-(Boc)-L-homoallylglycyl)-N-(2,4-dimethoxybenzyl)-L-homoallylglycine methyl ester

N-(N-(Boc)-L-homoallylglycyl)-N-(2-hydroxy-4-methoxybenzyl)-L-homoallylglycine methyl ester

N-(N-(Boc)-L-homoallylglycyl)-N-(2,4-dimethoxybenzyl)-L-allylglycine methyl ester

(S)-2-tert-butoxycarbonylamino-hex-5-enoic acid methyl ester

Refernces

• 1、 Vitkovska, Viktorija,Zogota, Rimants,Kalnins, Toms,Zelencova, Diana,Suna, Edgars. "Aliphatic chain-containing macrocycles as diazonamide A analogs". . p. 586 - 602. Retrieved 2020/06/10.
• 2、 Francisco Hilário, Flaviane,Traoré, Mohamed Dit Mady,Zwick, Vincent,Berry, Laurence,Sim?es-Pires, Claudia A.,Cuendet, Muriel,Fantozzi, Nicolas,Pereira De Freitas, Rossimiriam,Maynadier, Marjorie,Wein, Sharon,Vial, Henri,Wong, Yung-Sing. "Synthesis of an Uncharged Tetra-cyclopeptide Acting as a Transmembrane Carrier: Enhanced Cellular and Nuclear Uptake". supporting information. p. 612 - 615. Retrieved 2017/02/10.