(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

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Chemical Name:(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
CAS No.:1027532-24-6
Molecular Formula:C₄₆H₅₂N₂O₉Si
Molecular Weight:805.012
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 21 articles about (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 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: 100.0%

: 143164-84-5
3-<(S)-2-(benzyloxycarbonylamino)-2-(trimethylsilylethoxycarbonyl)ethyl>-3'-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)-(R)-1-hydroxyethyl>-4,4'-dibenzyloxybiphenyl

: 1027532-24-6
(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

Guidance literature:: With hydrogenchloride; In 1,4-dioxane; for 0.5h; Ambient temperature;
DOI:10.1039/c39920000951

Reference yield:

: 121124-94-5
2-benzyloxy-5-bromobenzaldehyde

: 1027532-24-6
(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

Guidance literature:: Multi-step reaction with 9 steps

1: 1) Sn(OTf)2, N-ethylpiperidine / 1) THF, -78 deg C, 90 min, 2) 2 h

2: 90 percent / MeMgBr / diethyl ether; CH₂Cl₂ / 0.05 h / 0 °C

3: 90 percent / DMAP / CH₂Cl₂ / 0.17 h

4: 30percent H₂O₂, HCO₂H / CH₂Cl₂ / 0.5 h / 0 °C

5: 2) 2M Na₂CO₃ / 1) Pd(PPh₃)4 / 1) THF, 1 h, reflux, 2) 24 h, reflux

6: 80 percent / Cs₂CO₃ / methanol / 2 h / Ambient temperature

7: 95 percent / tetramethylguanidine / tetrahydrofuran / 1) -70 to -30 deg C, 5 h, 2) -30 deg C, 2 d, 3) RT, 15 h

8: 85 percent / H₂ / (R,R)-BF₄ / methanol; CH₂Cl₂ / 48 h / 2250.2 Torr / Ambient temperature

9: 6M HCl / dioxane; CH₂Cl₂ / 0.5 h / Ambient temperature

With 1-ethyl-piperidine; hydrogenchloride; dmap; tin(II) trifluoromethanesulfonate; formic acid; 1,1,3,3-tetramethylguanidine; methylmagnesium bromide; hydrogen; dihydrogen peroxide; sodium carbonate; caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; (R,R)-⁺BF4^-; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane;
DOI:10.1055/s-1992-26351

Reference yield:

: 146335-33-3
(R)-5-(2-benzyloxy-5-bromo)phenyl (S)-4-(methoxycarbonyl)oxazolidin-2-thione

: 1027532-24-6
(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

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / DMAP / CH₂Cl₂ / 0.17 h

2: 30percent H₂O₂, HCO₂H / CH₂Cl₂ / 0.5 h / 0 °C

3: 2) 2M Na₂CO₃ / 1) Pd(PPh₃)4 / 1) THF, 1 h, reflux, 2) 24 h, reflux

4: 80 percent / Cs₂CO₃ / methanol / 2 h / Ambient temperature

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

6: 85 percent / H₂ / (R,R)-BF₄ / methanol; CH₂Cl₂ / 48 h / 2250.2 Torr / Ambient temperature

7: 6M HCl / dioxane; CH₂Cl₂ / 0.5 h / Ambient temperature

With hydrogenchloride; dmap; formic acid; 1,1,3,3-tetramethylguanidine; hydrogen; dihydrogen peroxide; sodium carbonate; caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; (R,R)-⁺BF4^-; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;
DOI:10.1055/s-1992-26351