(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

Base Information

• Chemical Name: (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
• CAS No.: 579469-85-5
• Molecular Formula: C₅₃H₇₁N₃O₁₂Si
• Molecular Weight: 970.245

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 15 articles about (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 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: 90.0%

L-isoleucine benzyl ester (42406-72-4) + 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) → (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 (579469-85-5)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25 ℃;

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

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (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 (579469-85-5)

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: 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

9.1: 90 percent / EDCI; HOAt; NAHCO₃ / dimethylformamide / 25 °C

With chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; 1-hydroxy-7-aza-benzotriazole; Trimethyl borate; tert.-butyl lithium; isopropylmagnesium chloride; chloroformic acid ethyl ester; sodium hydride; sodium hydrogencarbonate; sodium carbonate; periodic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 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) → (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 (579469-85-5)

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: 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

9.1: 90 percent / EDCI; HOAt; NAHCO₃ / dimethylformamide / 25 °C

With chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; 1-hydroxy-7-aza-benzotriazole; Trimethyl borate; tert.-butyl lithium; isopropylmagnesium chloride; chloroformic acid ethyl ester; sodium hydride; sodium hydrogencarbonate; sodium carbonate; periodic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 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:

L-isoleucine benzyl ester

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

di-tert-butyl dicarbonate

3-Iodo-L-tyrosine

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