3-[5'-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-3'-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-2-tert-butoxycarbonylamino-propionic acid

Base Information

• Chemical Name: 3-[5'-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-3'-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-2-tert-butoxycarbonylamino-propionic acid
• CAS No.: 579469-84-4
• Molecular Formula: C₄₀H₅₄N₂O₁₁Si
• Molecular Weight: 766.961
• Mol file: 579469-84-4.mol

Synonyms:3-[5'-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-3'-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-2-tert-butoxycarbonylamino-propionic acid

Chemical Property of 3-[5'-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-3'-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-2-tert-butoxycarbonylamino-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[5'-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-3'-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-2-tert-butoxycarbonylamino-propionic acid

There total 15 articles about 3-[5'-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-3'-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-2-tert-butoxycarbonylamino-propionic acid 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: 61.0%

2-benzyloxycarbonylamino-3-[5'-(2-tert-butoxycarbonylamino-3-hydroxy-propyl)-5-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-propionic acid methyl ester (622336-95-2) → 3-[5'-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-3'-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-2-tert-butoxycarbonylamino-propionic acid (579469-84-4)

Guidance literature:

With chromium(VI) oxide; periodic acid; In water; acetonitrile; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(03)00856-6

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 3-[5'-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-3'-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-2-tert-butoxycarbonylamino-propionic acid (579469-84-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 99 percent / NaHCO₃ / dioxane; H₂O / 18 h / 25 °C

2.1: 78 percent / NaH / dimethylformamide; tetrahydrofuran / 72 h / 25 °C

3.1: 82 percent / EtOCOCl; NaBH₄ / tetrahydrofuran; methanol / 0.33 h / 0 °C

4.1: 92 percent / i-Pr₂NEt / CH₂Cl₂ / 8 h / 25 °C

5.1: 99 percent / i-PrMgCl; t-BuLi; (MeO)3B / tetrahydrofuran / 1 h / -78 - 25 °C

6.1: 95 percent / Na₂CO₃; (o-tolyl)3P / Pd₂(dba)3 / toluene; methanol / 0.25 h / 85 °C

7.1: HCl / ethyl acetate / 0.5 h / -10 °C

7.2: 69 percent / NaHCO₃ / tetrahydrofuran; H₂O

8.1: 61 percent / CrO₃; periodic acid / acetonitrile; H₂O / 1 h / 0 °C

With chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; Trimethyl borate; tert.-butyl lithium; isopropylmagnesium chloride; chloroformic acid ethyl ester; sodium hydride; sodium hydrogencarbonate; sodium carbonate; periodic acid; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4039(03)00856-6

Reference yield:

3-Iodo-L-tyrosine (70-78-0) → 3-[5'-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-3'-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-2-tert-butoxycarbonylamino-propionic acid (579469-84-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 99 percent / NaHCO₃ / dioxane; H₂O / 18 h / 25 °C

2.1: 78 percent / NaH / dimethylformamide; tetrahydrofuran / 72 h / 25 °C

3.1: 82 percent / EtOCOCl; NaBH₄ / tetrahydrofuran; methanol / 0.33 h / 0 °C

4.1: 92 percent / i-Pr₂NEt / CH₂Cl₂ / 8 h / 25 °C

5.1: 99 percent / i-PrMgCl; t-BuLi; (MeO)3B / tetrahydrofuran / 1 h / -78 - 25 °C

6.1: 95 percent / Na₂CO₃; (o-tolyl)3P / Pd₂(dba)3 / toluene; methanol / 0.25 h / 85 °C

7.1: HCl / ethyl acetate / 0.5 h / -10 °C

7.2: 69 percent / NaHCO₃ / tetrahydrofuran; H₂O

8.1: 61 percent / CrO₃; periodic acid / acetonitrile; H₂O / 1 h / 0 °C

With chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; Trimethyl borate; tert.-butyl lithium; isopropylmagnesium chloride; chloroformic acid ethyl ester; sodium hydride; sodium hydrogencarbonate; sodium carbonate; periodic acid; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4039(03)00856-6

upstream raw materials:

2-benzyloxycarbonylamino-3-[5'-(2-tert-butoxycarbonylamino-3-hydroxy-propyl)-5-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-propionic acid methyl ester

di-tert-butyl dicarbonate

3-Iodo-L-tyrosine

L-3-(3-acetyl-4-hydroxyphenyl)-N-(benzyloxycarbonyl)alanine methyl ester

Downstream raw materials:

(2S,3S)-2-{(S)-3-[5'-((S)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-3'-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-2-tert-butoxycarbonylamino-propionylamino}-3-methyl-pentanoic acid benzyl ester