2-{[2-(5-benzyloxy-2-tert-butoxycarbonylamino-pentanoylamino)-3-phenyl-propionyl]-methyl-amino}-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid methyl ester

Base Information

• Chemical Name: 2-{[2-(5-benzyloxy-2-tert-butoxycarbonylamino-pentanoylamino)-3-phenyl-propionyl]-methyl-amino}-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid methyl ester
• CAS No.: 848780-47-2
• Molecular Formula: C₄₃H₆₁N₃O₈Si
• Molecular Weight: 776.058
• Mol file: 848780-47-2.mol

Synonyms:2-{[2-(5-benzyloxy-2-tert-butoxycarbonylamino-pentanoylamino)-3-phenyl-propionyl]-methyl-amino}-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid methyl ester

Chemical Property of 2-{[2-(5-benzyloxy-2-tert-butoxycarbonylamino-pentanoylamino)-3-phenyl-propionyl]-methyl-amino}-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{[2-(5-benzyloxy-2-tert-butoxycarbonylamino-pentanoylamino)-3-phenyl-propionyl]-methyl-amino}-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid methyl ester

There total 13 articles about 2-{[2-(5-benzyloxy-2-tert-butoxycarbonylamino-pentanoylamino)-3-phenyl-propionyl]-methyl-amino}-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid methyl 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: 24.0%

(S)-5-Benzyloxy-2-tert-butoxycarbonylamino-pentanoic acid (148529-07-1) + (S)-2-[((S)-2-Amino-3-phenyl-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid methyl ester; hydrochloride → Boc-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr-OMe (370867-51-9) + 2-{[2-(5-benzyloxy-2-tert-butoxycarbonylamino-pentanoylamino)-3-phenyl-propionyl]-methyl-amino}-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid methyl ester (848780-47-2)

Guidance literature:

With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.12.009

Reference yield:

Boc-Tyr-OH (3978-80-1) → 2-{[2-(5-benzyloxy-2-tert-butoxycarbonylamino-pentanoylamino)-3-phenyl-propionyl]-methyl-amino}-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid methyl ester (848780-47-2)

Guidance literature:

Multi-step reaction with 8 steps

1: imidazole / dimethylformamide / 13 h / 0 - 20 °C

2: 3.6 g / K₂CO₃; H₂O / tetrahydrofuran; methanol / 48 h / 20 °C

3: 84 percent / t-BuLi / tetrahydrofuran; pentane / 19 h / 0 - 20 °C

4: 94 percent / KHCO₃ / dimethylformamide / 13 h / 0 - 20 °C

5: HCl / ethyl acetate / 1 h

6: 72 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; triethylamine / CH₂Cl₂ / 15 h / 4 °C

7: HCl / ethyl acetate

8: 16 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide

With 1H-imidazole; hydrogenchloride; diethyl cyanophosphonate; water; tert.-butyl lithium; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium carbonate; potassium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; pentane;

DOI:10.1016/j.tet.2004.12.009

Reference yield:

benzyl bromide (100-39-0) → 2-{[2-(5-benzyloxy-2-tert-butoxycarbonylamino-pentanoylamino)-3-phenyl-propionyl]-methyl-amino}-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid methyl ester (848780-47-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / Ag₂O / diethyl ether / 14 h

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

3: 16 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide

With lithium hydroxide; diethyl cyanophosphonate; triethylamine; silver(l) oxide; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.12.009

upstream raw materials:

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

Boc-Tyr-OH

benzyl bromide

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

Downstream raw materials:

cyclo[Boc-(S)-Thr-(S)-Phe-(S)-Phs-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile]

cyclo[Boc-(S)-Thr-(S)-Phe-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile]

cyclo[Troc-(S)-Thr-(S)-Phe-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile]

Troc-(S)-Thr[Boc-(S)-Phs(Bn)-(S)-Phe-(S)-NMe-Tyr-(S)-Ile]-(S)-Phe-OAllyl