4,4'-dibenzyloxy-3-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)-(R)-1-hydroxyethyl>-3'-<(Z)-2-(benzyloxycarbonylamino)-2-(trimethylsilylethoxycarbonyl)vinyl>biphenyl

Base Information

• Chemical Name: 4,4'-dibenzyloxy-3-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)-(R)-1-hydroxyethyl>-3'-<(Z)-2-(benzyloxycarbonylamino)-2-(trimethylsilylethoxycarbonyl)vinyl>biphenyl
• CAS No.: 143164-83-4
• Molecular Formula: C₅₁H₅₈N₂O₁₁Si
• Molecular Weight: 903.114

Synonyms:4,4'-dibenzyloxy-3-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)-(R)-1-hydroxyethyl>-3'-<(Z)-2-(benzyloxycarbonylamino)-2-(trimethylsilylethoxycarbonyl)vinyl>biphenyl

Chemical Property of 4,4'-dibenzyloxy-3-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)-(R)-1-hydroxyethyl>-3'-<(Z)-2-(benzyloxycarbonylamino)-2-(trimethylsilylethoxycarbonyl)vinyl>biphenyl

Chemical Property:

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Technology Process of 4,4'-dibenzyloxy-3-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)-(R)-1-hydroxyethyl>-3'-<(Z)-2-(benzyloxycarbonylamino)-2-(trimethylsilylethoxycarbonyl)vinyl>biphenyl

There total 22 articles about 4,4'-dibenzyloxy-3-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)-(R)-1-hydroxyethyl>-3'-<(Z)-2-(benzyloxycarbonylamino)-2-(trimethylsilylethoxycarbonyl)vinyl>biphenyl 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: 95.0%

2-(trimethylsilyl)ethyl α-(dimethoxyphosphoryl)-N-(benzyloxycarbonyl)glycinate (134038-88-3) + 4,4'-dibenzyloxy-3-<(S)-2-(tert-butoxycarbonylamino)-2-methoxycarbonyl-(R)-1-hydroxyethyl>biphenyl-3'-carbaldehyde (143164-82-3) → 4,4'-dibenzyloxy-3-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)-(R)-1-hydroxyethyl>-3'-<(Z)-2-(benzyloxycarbonylamino)-2-(trimethylsilylethoxycarbonyl)vinyl>biphenyl (143164-83-4)

Guidance literature:

With 1,1,3,3-tetramethylguanidine; In tetrahydrofuran; 1) -70 to -30 deg C, 5 h, 2) -30 deg C, 2 d, 3) RT, 15 h;

DOI:10.1055/s-1992-26351

Reference yield: 80.0%

N-benzyloxycarbonyl(dimethoxyphosphoryl) glycine trimethylsilylethyl ester + 4,4'-dibenzyloxy-3-<(S)-2-(tert-butoxycarbonylamino)-2-methoxycarbonyl-(R)-1-hydroxyethyl>biphenyl-3'-carbaldehyde (143164-82-3) → 4,4'-dibenzyloxy-3-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)-(R)-1-hydroxyethyl>-3'-<(Z)-2-(benzyloxycarbonylamino)-2-(trimethylsilylethoxycarbonyl)vinyl>biphenyl (143164-83-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -78 ℃; for 15h;

DOI:10.1039/c39920000951

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 4,4'-dibenzyloxy-3-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)-(R)-1-hydroxyethyl>-3'-<(Z)-2-(benzyloxycarbonylamino)-2-(trimethylsilylethoxycarbonyl)vinyl>biphenyl (143164-83-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 81 percent / 1M aq. KHCO₃ / 24 h / Ambient temperature

2: 91 percent / 1M aq. NaOH / dioxane / 15 h / Ambient temperature

3: 1) n-BuLi / 1) THF, hexane, -70 deg C, 20 min, 2a) -70 deg C to RT, 2b) RT, 15 h

4: H₂ / <(R)-(RuCl(p-cymene)BINAP>Cl / methanol; CH₂Cl₂ / 72 h / 50 °C / 37503 Torr

5: 97 percent / aq. HOAc / 3 h / 50 °C

6: 95 percent / tetramethylguanidine / tetrahydrofuran / 1) -70 to -30 deg C, 5 h, 2) -30 deg C, 2 d, 3) RT, 15 h

With sodium hydroxide; n-butyllithium; 1,1,3,3-tetramethylguanidine; hydrogen; potassium hydrogencarbonate; acetic acid; ((+)-(1R)-[1,1'-binaphthalene]-2,2'-diylbis[diphenylphosphine-κP])chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium(1+) chloride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1055/s-1992-26351

upstream raw materials:

2-(trimethylsilyl)ethyl α-(dimethoxyphosphoryl)-N-(benzyloxycarbonyl)glycinate

3-(4,4'-Bis-benzyloxy-3'-formyl-biphenyl-3-yl)-2-tert-butoxycarbonylamino-3-hydroxy-propionic acid methyl ester

4,4'-dibenzyloxy-3-<(S)-2-(tert-butoxycarbonylamino)-2-methoxycarbonyl-(R)-1-hydroxyethyl>biphenyl-3'-carbaldehyde

di-tert-butyl dicarbonate

Downstream raw materials:

3-<(S)-2-(benzyloxycarbonylamino)-2-(trimethylsilylethoxycarbonyl)ethyl>-3'-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)-(R)-1-hydroxyethyl>-4,4'-dibenzyloxybiphenyl

(2S,3R)-2-Amino-3-{4,4'-bis-benzyloxy-3'-[(S)-2-benzyloxycarbonylamino-2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-biphenyl-3-yl}-3-hydroxy-propionic acid methyl ester

(2S,3R)-2-((2S,4R)-5-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-hydroxy-pentanoylamino)-3-[4,4'-bis-benzyloxy-3'-((S)-2-benzyloxycarbonylamino-2-pentafluorophenyloxycarbonyl-ethyl)-biphenyl-3-yl]-3-hydroxy-propionic acid methyl ester

(7R,8S,11S,14S)-5,17-Bis-benzyloxy-14-benzyloxycarbonylamino-11-((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-7-hydroxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽¹⁹⁾,2⁽²¹⁾,3,5,16⁽²⁰⁾,17-hexaene-8-carboxylic acid

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