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

Base Information

• Chemical Name: (S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-3-[5'-((S)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-5-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-propionic acid methyl ester
• CAS No.: 579469-89-9
• Molecular Formula: C₄₆H₆₇N₃O₁₁Si
• Molecular Weight: 866.137

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

Chemical Property of (S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-3-[5'-((S)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-5-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-propionic acid methyl ester

Chemical Property:

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Technology Process of (S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-3-[5'-((S)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-5-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-propionic acid methyl ester

There total 16 articles about (S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-3-[5'-((S)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-5-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-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: 69.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-3-[5'-((S)-2-tert-butoxycarbonylamino-3-methoxymethoxy-propyl)-5-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-propionic acid methyl ester (579469-88-8) → (S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-3-[5'-((S)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-5-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-propionic acid methyl ester (579469-89-9)

Guidance literature:

(S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-3-[5'-((S)-2-tert-butoxycarbonylamino-3-methoxymethoxy-propyl)-5-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-propionic acid methyl ester; With hydrogenchloride; In ethyl acetate; at -10 ℃; for 0.5h;

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

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

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-3-[5'-((S)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-5-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-propionic acid methyl ester (579469-89-9)

Guidance literature:

Multi-step reaction with 9 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: 99 percent / H₂ / Pd/C / methanol / 15 h / 25 °C / 760 Torr

8.1: 93 percent / EDCI; HOAt / dimethylformamide

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

9.2: 69 percent / NaHCO₃ / tetrahydrofuran; H₂O

With hydrogenchloride; sodium tetrahydroborate; 1-hydroxy-7-aza-benzotriazole; Trimethyl borate; hydrogen; tert.-butyl lithium; isopropylmagnesium chloride; chloroformic acid ethyl ester; sodium hydride; sodium hydrogencarbonate; sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; palladium on activated charcoal; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

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

Reference yield:

3-Iodo-L-tyrosine (70-78-0) → (S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-3-[5'-((S)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-5-(tert-butyl-dimethyl-silanyloxy)-6,2'-dimethoxy-biphenyl-3-yl]-propionic acid methyl ester (579469-89-9)

Guidance literature:

Multi-step reaction with 9 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: 99 percent / H₂ / Pd/C / methanol / 15 h / 25 °C / 760 Torr

8.1: 93 percent / EDCI; HOAt / dimethylformamide

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

9.2: 69 percent / NaHCO₃ / tetrahydrofuran; H₂O

With hydrogenchloride; sodium tetrahydroborate; 1-hydroxy-7-aza-benzotriazole; Trimethyl borate; hydrogen; tert.-butyl lithium; isopropylmagnesium chloride; chloroformic acid ethyl ester; sodium hydride; sodium hydrogencarbonate; sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; palladium on activated charcoal; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

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

upstream raw materials:

di-tert-butyl dicarbonate

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

3-Iodo-L-tyrosine

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

Downstream raw materials:

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

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