2-tert-butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester

Base Information

• Chemical Name: 2-tert-butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester
• CAS No.: 105589-11-5
• Molecular Formula: C₂₀H₂₇NO₈
• Molecular Weight: 409.436
• Mol file: 105589-11-5.mol

Synonyms:2-tert-butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester

Chemical Property of 2-tert-butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-tert-butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester

There total 1 articles about 2-tert-butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester 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:

Boc-Glu-OBn (30924-93-7) + chloroformic acid ethyl ester (541-41-3) → 2-tert-butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester (105589-11-5)

Guidance literature:

With triethylamine; In tetrahydrofuran; at -10 ℃; for 0.166667h;

DOI:10.1021/jm9803727

Reference yield:

2-tert-butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester (105589-11-5) → (S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester (91229-97-9)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -10 - 0 ℃; for 0.333333h;

DOI:10.1021/jm9803727

Reference yield:

2-tert-butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester (105589-11-5) → phosphoric acid dibenzyl ester 2-benzyloxy-2-[2,15-dibenzyl-8-sec-butyl-21-hydroxy-5-(4-hydroxy-benzyl)-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentaaza-bicyclo[16.3.1]docos-12-ylcarbamoyl]-ethyl ester (370867-66-6)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 2.86 g / NaBH₄ / tetrahydrofuran; H₂O / 3 h / -10 - 20 °C

2.1: 82 percent / Ag₂O / diethyl ether / 14 h

3.1: LiOH / tetrahydrofuran; H₂O / 12 h / 20 °C

4.1: 60 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 19 h / 0 - 20 °C

5.1: LiOH / tetrahydrofuran; H₂O / 2 h / 0 - 20 °C

6.1: 77 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 15 h / 0 - 20 °C

7.1: 75 percent / imidazole / dimethylformamide / 13 h / 0 - 20 °C

8.1: morpholine / (PPh₃)4Pd / tetrahydrofuran / 2 h

9.1: HCl / dioxane / 1.5 h / 0 °C

10.1: 84 percent / pentafluorophenyl diphenylphosphinate; N,N-diisopropylethylamine / CH₂Cl₂ / 17 h / 20 °C

11.1: zinc; acetic acid / tetrahydrofuran / 4.5 h

11.2: 77 percent / triethylamine / tetrahydrofuran / 6 h / 0 - 20 °C

12.1: 100 percent / H₂ / Pd(OH)2 / ethyl acetate / 3 h / 20 °C / 760 Torr

13.1: HCl / dioxane / 2.5 h / 0 - 20 °C

14.1: 21 mg / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 13 h / 0 - 20 °C

15.1: 1-hydroxy-1,2-benzodioxol-3(1H)-one 1-oxide / dimethylsulfoxide

15.2: 68 percent / n-Bu₄NF / tetrahydrofuran

With morpholine; 1H-imidazole; hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; diethyl cyanophosphonate; pentafluorophenyl diphenyl-phosphinate; hydrogen; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; silver(l) oxide; zinc; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.12.009

upstream raw materials:

Boc-Glu-OBn

chloroformic acid ethyl ester

Downstream raw materials:

(S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester

(S)-5-Benzyloxy-2-tert-butoxycarbonylamino-pentanoic acid

benzyl (S)-2-tert-butoxycarbonylamino-5-benzyloxypentanoate

Boc-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr-OMe